CN116023354A

CN116023354A - Light-emitting element and amine compound for light-emitting element

Info

Publication number: CN116023354A
Application number: CN202211265402.5A
Authority: CN
Inventors: 今田一郎; 上野雅嗣
Original assignee: Samsung Display Co Ltd
Current assignee: Samsung Display Co Ltd
Priority date: 2021-10-25
Filing date: 2022-10-17
Publication date: 2023-04-28
Also published as: KR20230059895A; US20230129941A1

Abstract

The present application relates to an amine compound represented by formula 1 and a light-emitting element including a first electrode, a second electrode provided on the first electrode, and at least one functional layer provided between the first electrode and the second electrode and containing the amine compound represented by formula 1. The light emitting element can exhibit high light emitting efficiency and long service life characteristics. [ 1 ]]

Wherein the variables in formula 1 are the same as defined in the specification.

Description

Light-emitting element and amine compound for light-emitting element

Cross Reference to Related Applications

The present application claims priority and rights of korean patent application No. 10-2021-0143043, filed on the korean intellectual property office on the 10 th month 25 of 2021, the entire contents of which are incorporated herein by reference.

Technical Field

The present disclosure relates to a light emitting element including a novel amine compound in a hole transport region and the amine compound.

Background

Active development of organic electroluminescent display devices and the like as image display devices is continuously being conducted. An organic electroluminescent display device or the like is a display device including a so-called self-light-emitting display element in which holes and electrons injected from a first electrode and a second electrode, respectively, are recombined in a light-emitting layer, so that a light-emitting material in the light-emitting layer emits light to realize display.

In the application of light emitting elements to display devices, there is a demand for low driving voltage, high light emitting efficiency, and long service life, and there is a demand for continuous development of materials for light emitting elements capable of stably obtaining such characteristics.

In order to realize a high-efficiency light-emitting element, there is also a need for developing a material for a hole transport region for suppressing exciton energy diffusion in a light-emitting layer.

It should be appreciated that this background section is intended to provide, in part, a useful background for understanding the technology. However, this background section may also include concepts, concepts or cognition that were not known or understood by those skilled in the relevant art prior to the corresponding effective application date of the subject matter disclosed herein.

Disclosure of Invention

The present disclosure provides a light emitting element exhibiting excellent light emitting efficiency and long service life characteristics.

The present disclosure also provides an amine compound that is a material for a light-emitting element having high light-emitting efficiency and long-life characteristics.

Embodiments provide amine compounds that may be represented by formula 1:

[ 1]

[ 2]

In formula 1, ar ₁ May be a substituted or unsubstituted aryl group having 6 to 40 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 40 ring-forming carbon atoms, other than a phenanthryl group; r is R ₁ To R ₄ May each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 ring-forming carbon atoms, or may be a single bond forming a ring by bonding to the group represented by formula 2; r is as follows ₁ And R is ₂ R and/or R of (C) ₃ And R is ₄ May be bonded to the group represented by formula 2 to form a ring. In formula 2, X may be O, S, N (R ₁₀ ) Or C (R) ₁₁ )(R ₁₂ ) And a and b each represent R in formula 1 ₁ To R ₄ Any one of the keys. In formula 1 and formula 2, R ₅ To R ₁₂ May each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 40 ring-forming carbon atoms; a and b may each independently be an integer from 0 to 2; c and d may each independently be an integer from 0 to 7; and e may be an integer from 0 to 4.

In an embodiment, the amine compound represented by formula 1 may be represented by any one of formulas 1-1 to 1-3:

[ 1-1]

[ 1-2]

[ 1-3]

In the formulae 1 to 3, X ₁ And X ₂ Can each independently be O, S, N (R ₁₀ ) Or C (R) ₁₁ )(R ₁₂ ) The method comprises the steps of carrying out a first treatment on the surface of the e1 and e2 may each independently be an integer from 0 to 4; r is as follows ₉₁ And R is ₉₂ May each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 40 ring-forming carbon atoms. In the formulae 1-1 to 1-3, ar ₁ 、X、R ₁ 、R ₂ 、R ₅ To R ₁₂ And a to e are the same as defined in

formulae

1 and 2.

In embodiments, in formulas 1-3, X ₁ And X ₂ May be the same.

In an embodiment, the group represented by formula 2 may be represented by any one of formulas 2-1 to 2-5:

in the formulae 2-1 to 2-5, R ₉ E, a and b are the same as defined in formula 2.

In an embodiment, in formula 1, ar ₁ Can be substituted or unsubstitutedA substituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzothiophene group, or a substituted or unsubstituted dibenzofuran group.

In embodiments, in

formulas

1 and 2, R ₁ To R ₉ May be a deuterium atom or a substituent comprising a deuterium atom; and/or Ar ₁ May be a substituent comprising a deuterium atom.

In an embodiment, the amine compound represented by formula 1 may be a monoamine compound.

In embodiments, the amine compound may be selected from compound group 1 explained below.

Another embodiment provides a light emitting element that may include a first electrode, a second electrode disposed on the first electrode, and at least one functional layer disposed between the first electrode and the second electrode and including the amine compound according to the embodiment.

In an embodiment, the at least one functional layer may include a light emitting layer, a hole transport region disposed between the first electrode and the light emitting layer, and an electron transport region disposed between the light emitting layer and the second electrode; and the hole transport region may contain the amine compound.

In an embodiment, the hole transport region may include at least one of a hole injection layer, a hole transport layer, and an electron blocking layer; and at least one of the hole injection layer, the hole transport layer, and the electron blocking layer may contain the amine compound.

In an embodiment, the hole transport region may include a first hole transport layer and a second hole transport layer sequentially stacked between the first electrode and the light emitting layer; the first hole transport layer and the second hole transport layer may comprise different hole transport materials; and the second hole transport layer may contain the amine compound.

In embodiments, the light emitting layer may include a compound represented by formula E-1 explained below.

In an embodiment, the light emitting element may further include a capping layer disposed on the second electrode, wherein the capping layer may have a refractive index equal to or greater than about 1.6.

Drawings

The accompanying drawings are included to provide a further understanding of the embodiments and are incorporated in and constitute a part of this specification. The drawings illustrate embodiments of the present disclosure and their principles. The above and other aspects and features of the present disclosure will become more apparent by describing in detail embodiments thereof with reference to the attached drawings in which:

fig. 1 is a plan view illustrating a display device according to an embodiment;

fig. 2 is a schematic cross-sectional view of a display device according to an embodiment;

fig. 3 is a schematic cross-sectional view illustrating a light emitting element according to an embodiment;

fig. 4 is a schematic cross-sectional view illustrating a light emitting element according to an embodiment;

fig. 5 is a schematic cross-sectional view illustrating a light emitting element according to an embodiment;

fig. 6 is a schematic cross-sectional view illustrating a light emitting element according to an embodiment;

Fig. 7 is a schematic cross-sectional view illustrating a light emitting element according to an embodiment;

fig. 8 is a schematic cross-sectional view illustrating a display device according to an embodiment;

fig. 9 is a schematic cross-sectional view illustrating a display device according to an embodiment;

fig. 10 is a schematic cross-sectional view illustrating a display device according to an embodiment; and

fig. 11 is a schematic cross-sectional view illustrating a display device according to an embodiment.

Detailed Description

The present disclosure will now be described more fully hereinafter with reference to the accompanying drawings, in which embodiments are shown. This disclosure may, however, be embodied in different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the scope of the disclosure to those skilled in the art.

In the drawings, the size, thickness, proportion and dimensions of the elements may be exaggerated for convenience of description and for clarity. Like numbers refer to like elements throughout.

In the description, it will be understood that when an element (or region, layer, component, etc.) is referred to as being "on," "connected to," or "coupled to" another element, it can be directly on, connected to, or coupled to the other element or intervening elements may be present therebetween. In a similar sense, when an element (or region, layer, component, etc.) is referred to as "overlying" another element, it can directly overlie the other element or one or more intervening elements may be present therebetween.

In the description, when an element is "directly on," "directly connected to," or "directly coupled to" another element, there are no intervening elements present. For example, "directly on" may mean that two layers or elements are provided without additional elements, such as adhesive elements, therebetween.

As used herein, references to the singular, such as "a," "an," and "the" are intended to include the plural as well, unless the context clearly indicates otherwise.

As used herein, the term "and/or" includes any and all combinations of one or more of the associated listed items. For example, "a and/or B" may be understood to mean "A, B, or a and B". The terms "and" or "may be used in the sense of a conjunctive or disjunctive and are understood to be equivalent to" and/or ".

For the purposes of their meaning and explanation, the term "at least one (species)" in the group of "is intended to include the meaning of" at least one (species) selected from the group of "in. For example, "at least one of a and B" may be understood to mean "A, B, or a and B". When before a list of elements, at least one of the terms "..the term" modifies an entire list of elements without modifying individual elements of the list.

It will be understood that, although the terms first, second, etc. may be used herein to describe various elements, these elements should not be limited by these terms. These terms are only used to distinguish one element from another element. Thus, a first element could be termed a second element without departing from the teachings of the present disclosure. Similarly, a second element may be termed a first element without departing from the scope of the present disclosure.

For ease of description, spatially relative terms "below," "under," "lower," "above," "upper," and the like may be used herein to describe one element or component's relationship to another element or component as illustrated in the figures. It will be understood that spatially relative terms are intended to encompass different orientations of the device in use or operation in addition to the orientation depicted in the figures. For example, in the case where the apparatus illustrated in the drawings is turned over, an apparatus located "below" or "beneath" another apparatus may be placed "above" the other apparatus. Thus, the exemplary term "below" may include both a lower position and an upper position. The device may also be oriented in other directions and, therefore, spatially relative terms may be construed differently depending on the direction.

The term "about" or "approximately" as used herein includes the specified values and means within an acceptable range of deviation of the values as determined by one of ordinary skill in the art taking into account the relevant measurements and the errors associated with the measurement of the quantities (i.e., limitations of the measurement system). For example, "about" may mean within one or more standard deviations, or within ±20%, 10% or ±5% of the specified value.

It should be understood that the terms "comprises," "comprising," "includes," "including," "containing," "having," "contains," "containing," "including," "containing," "comprising," or the like are intended to specify the presence of stated features, integers, steps, operations, elements, components, or groups thereof, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, or groups thereof.

Unless defined or implied otherwise herein, all terms (including technical and scientific terms) used have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning that is consistent with their meaning in the context of the relevant art and will not be interpreted in an idealized or overly formal sense unless expressly so defined herein.

In the specification, the term "substituted or unsubstituted" may mean a group substituted with at least one substituent selected from the group consisting of a deuterium atom, a halogen atom, a cyano group, a nitro group, an amino group, a silyl group, an oxo group, a thio group, a sulfinyl group, a sulfonyl group, a carbonyl group, a boron group, a phosphine oxide group, a phosphine sulfide group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, a hydrocarbon ring group, an aryl group, and a heterocyclic group. Each of the substituents listed above may be substituted or unsubstituted per se. For example, a biphenyl group may be interpreted as an aryl group, or it may be interpreted as a phenyl group substituted with a phenyl group.

In the specification, the term "bonded to an adjacent group to form a ring" may mean a group bonded to an adjacent group to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring. The hydrocarbon ring may be an aliphatic hydrocarbon ring or an aromatic hydrocarbon ring. The heterocycle may be aliphatic or aromatic. The hydrocarbon ring and the heterocyclic ring may each independently be monocyclic or polycyclic. The ring formed by the combination of adjacent groups may itself be linked to another ring to form a spiro structure.

In the specification, the term "adjacent group" may mean a substituent substituted at an atom directly connected to an atom substituted with a corresponding substituent, another substituent substituted at an atom substituted with a corresponding substituent, or a substituent three-dimensionally nearest to the corresponding substituent. For example, in 1, 2-dimethylbenzene, two methyl groups may be interpreted as "adjacent groups" to each other, and in 1, 1-diethylcyclopentane, two ethyl groups may be interpreted as "adjacent groups" to each other. For example, in 4, 5-dimethylfiil, two methyl groups may be interpreted as "adjacent groups" to each other.

In the specification, examples of the halogen atom may include a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

In the specification, the alkyl group may be linear, branched or cyclic. The number of carbon atoms in the alkyl group may be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Examples of the alkyl group may include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, an isobutyl group, a 2-ethylbutyl group, a 3, 3-dimethylbutyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a cyclopentyl group, a 1-methylpentyl group, a 3-methylpentyl group, a 2-ethylpentyl group, a 4-methyl-2-pentyl group, an n-hexyl group, a 1-methylhexyl group, a 2-ethylhexyl group, a 2-butylhexyl group, a cyclohexyl group, a 4-methylcyclohexyl group, a 4-tert-butylcyclohexyl group, an n-heptyl group, a 1-methylheptyl group, a 2, 2-dimethylheptyl group 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3, 7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl group, 2-hexylhexadecyl group, 2-octylhexadecyl group, n-heptadecyl group, n-octadecyl group, n-nonadecyl group, n-eicosyl group, 2-ethyleicosyl group, 2-butyleicosyl group, 2-hexyleicosyl group, 2-octyleicosyl group, n-heneicosyl group, n-docosyl group, n-tricosyl group, n-tetracosyl group, n-pentacosyl group, n-hexacosyl group, n-heptacosyl group, n-octacosyl group, n-nonacosyl group, n-triacontyl group, and the like, but the embodiment is not limited thereto.

In the specification, an alkenyl group may be a hydrocarbon group containing one or more than one carbon-carbon double bond at the middle or end of an alkyl group having 2 or more than 2 carbon atoms. The alkenyl group may be linear or branched. The number of carbon atoms in the alkenyl group is not particularly limited, but may be 2 to 30, 2 to 20, or 2 to 10. Examples of the alkenyl group may include a vinyl group, a 1-butenyl group, a 1-pentenyl group, a 1, 3-butadienyl group, a styryl group, a styrylvinyl group, and the like, but the embodiment is not limited thereto.

In the specification, the hydrocarbon ring group may be any functional group or substituent derived from an aliphatic hydrocarbon ring or an aromatic hydrocarbon ring. For example, the hydrocarbon ring group may be a saturated hydrocarbon ring group having 5 to 20 ring-forming carbon atoms.

In the specification, an aryl group may be any functional group or substituent derived from an aromatic hydrocarbon ring. The aryl group may be a monocyclic aryl group or a polycyclic aryl group. The number of ring-forming carbon atoms in the aryl group may be 6 to 30, 6 to 20 or 6 to 15. Examples of the aryl group may include a phenyl group, a naphthyl group, a fluorenyl group, an anthryl group, a phenanthryl group, a biphenyl group, a terphenyl group, a tetrabiphenyl group, a pentabiphenyl group, a hexabiphenyl group, a benzophenanthryl group, a pyrenyl group, a benzofluoranthenyl group, a,

A group, etc., but the embodiment is not limited thereto.

In the specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. Examples of substituted fluorenyl groups are as follows. However, the embodiment is not limited thereto.

In the specification, a heterocyclic group may be any functional group or substituent derived from a ring containing at least one of B, O, N, P, si and S as a heteroatom, and the number of heteroatoms in the heterocyclic group may be 1 to 10, for example 1, 2, 3, 4 or 5. The heterocyclic group may be an aliphatic heterocyclic group or an aromatic heterocyclic group. The aromatic heterocyclic group may be a heteroaryl group. The aliphatic heterocycle and the aromatic heterocycle may each independently be monocyclic or polycyclic.

In the specification, the heterocyclic group may contain at least one of B, O, N, P, si and S as a heteroatom. When the heterocyclic group contains two or more heteroatoms, the two or more heteroatoms may be the same as or different from each other. In the specification, the heterocyclic group may be a monocyclic group or a polycyclic group, and the heterocyclic group may be a heteroaryl group. The number of ring-forming carbon atoms in the heterocyclic group may be 2 to 30, 2 to 20 or 2 to 10.

In the specification, the aliphatic heterocyclic group may contain at least one of B, O, N, P, si and S as a heteroatom. The number of ring-forming carbon atoms in the aliphatic heterocyclic group may be 2 to 30, 2 to 20, or 2 to 10. Examples of the aliphatic heterocyclic group may include an oxetanyl group, a thietane group, a pyrrolidinyl group, a piperidinyl group, a tetrahydrofuranyl group, a tetrahydrothiophenyl group, a thietane group, a tetrahydropyran group, a 1, 4-dioxanyl group, and the like, but the embodiment is not limited thereto.

In the specification, the heteroaryl group may contain at least one of B, O, N, P, si and S as a heteroatom. When the heteroaryl group contains two or more heteroatoms, the two or more heteroatoms may be the same as or different from each other. Heteroaryl groups may be monocyclic or polycyclic. The number of ring-forming carbon atoms in the heterocyclic group may be 2 to 30, 2 to 20 or 2 to 10. Examples of heteroaryl groups may include thiophene groups, furan groups, pyrrole groups, imidazole groups, triazole groups, pyridine groups, bipyridine groups, pyrimidine groups, triazine groups, acridine groups, pyridazine groups, pyrazinyl groups, quinoline groups, quinazoline groups, quinoxaline groups, phenoxy groups, phthalazine groups, pyridopyrimidine groups, pyridopyrazine groups, pyrazinopyrazine groups, isoquinoline groups, indole groups, carbazole groups, N-arylcarbazole groups, N-heteroarylcarbazole groups, N-alkylcarbzole groups, benzoxazole groups, benzimidazole groups, benzothiazole groups, benzothiophene groups, dibenzothiophene groups, thiophene groups, benzofuran groups, phenanthroline groups, thiazole groups, isoxazole groups, oxazole groups, oxadiazole groups, thiadiazole groups, phenothiazine groups, dibenzothiophene groups, dibenzofuran groups, and the like, but embodiments are not limited thereto.

In the specification, the description of the aryl group described above may be applied to an arylene group, but the arylene group is a divalent group. The description of heteroaryl groups described above may be applied to heteroarylene groups, but heteroarylene groups are divalent groups.

In the specification, the boron group may be an alkyl boron group or an aryl boron group. Examples of the boron group may include trimethylboron group, triethylboron group, t-butyldimethylboro group, triphenylboron group, diphenylboron group, phenylboron group, and the like, but the embodiment is not limited thereto. For example, the alkyl groups in the alkyl boron groups may be the same as the alkyl groups as described above, and the aryl groups in the aryl boron groups may be the same as the aryl groups as described above.

In the specification, the silyl group may be an alkylsilyl group or arylsilyl group. Examples of the silyl group may include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like, but the embodiment is not limited thereto.

In the specification, the number of carbon atoms in the carbonyl group is not particularly limited, but may be 1 to 40, 1 to 30, or 1 to 20. For example, the carbonyl group may have one of structures as shown below, but is not limited thereto.

In the specification, the number of carbon atoms in the sulfinyl group and the number of carbon atoms in the sulfonyl group are not particularly limited, but may each be independently 1 to 30, 1 to 20, or 1 to 10. The sulfinyl group may be an alkylsulfinyl group or an arylsulfinyl group. The sulfonyl group may be an alkylsulfonyl group or an arylsulfonyl group.

In the specification, a thio group may be an alkylthio group or an arylthio group. The thio group may be a sulfur atom bonded to an alkyl group or an aryl group as defined above. Examples of the thio group may include a methylthio group, an ethylthio group, a propylthio group, a pentylthio group, a hexylthio group, an octylthio group, a dodecylthio group, a cyclopentylthio group, a cyclohexylthio group, a phenylthio group, a naphthylthio group, and the like, but the embodiment is not limited thereto.

In the specification, an oxy group may be an oxygen atom bonded to an alkyl group or an aryl group as defined above. The oxy group may be an alkoxy group or an aryloxy group. The alkoxy groups may be linear, branched or cyclic. The number of carbon atoms in the alkoxy group is not particularly limited, but may be, for example, 1 to 20 or 1 to 10. Examples of the oxy group may include methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, octyloxy, nonyloxy, decyloxy, benzyloxy, and the like. However, the embodiment is not limited thereto.

In the specification, the number of carbon atoms in the amine group is not particularly limited, but may be 1 to 30, 1 to 20, or 1 to 10. The amine groups may be alkyl amine groups or aryl amine groups. Examples of the amine group may include a methylamino group, a dimethylamino group, a phenylamino group, a diphenylamino group, a naphthylamine group, and a 9-methyl-anthracenyl amine group, but the embodiment is not limited thereto.

In the specification, the alkyl group in the alkylthio group, alkylsulfonyl group, alkylaryl group, alkylamino group, alkylboron group, alkylsilyl group or alkylamino group may be the same as the alkyl group as defined above.

In the specification, the aryl group in the aryloxy group, arylthio group, arylsulfonyl group, arylamino group, arylboron group, arylsilyl group or arylamino group may be the same as the aryl group as defined above.

In the specification, the linear bond may be a single bond.

In the description, symbols are used

And each represents a bonding site to an adjacent atom.

Hereinafter, a light emitting element and an amine compound according to an embodiment will be described with reference to the drawings.

Fig. 1 is a plan view illustrating an embodiment of a display device DD. Fig. 2 is a schematic cross-sectional view of a display device DD according to an embodiment. Fig. 2 is a schematic cross-sectional view taken along line I-I' of fig. 1.

The display device DD may include a display panel DP and an optical layer PP disposed on the display panel DP. The display panel DP may include light emitting elements ED-1, ED-2 and ED-3. The display device DD may comprise a plurality of light emitting elements ED-1, ED-2 and ED-3. The optical layer PP may be disposed on the display panel DP and may control light reflected at the display panel DP by external light. For example, the optical layer PP may include a polarizing layer or a color filter layer. Although not shown in the drawings, in an embodiment, the optical layer PP may be omitted from the display device DD.

The base substrate BL may be disposed on the optical layer PP. The base substrate BL may provide a base surface on which the optical layer PP is disposed. The base substrate BL may be a glass substrate, a metal substrate, a plastic substrate, or the like. However, the embodiment is not limited thereto, and the base substrate BL may include an inorganic layer, an organic layer, or a composite material layer. Although not shown in the drawings, in an embodiment, the base substrate BL may be omitted.

The display device DD according to the embodiment may further include a filling layer (not shown). A filler layer (not shown) may be disposed between the display element layer DP-ED and the base substrate BL. The filler layer (not shown) may be a layer of organic material. The filler layer (not shown) may include at least one of an acrylic-based resin, a silicone-based resin, and an epoxy-based resin.

The display panel DP may include a base layer BS, a circuit layer DP-CL provided on the base layer BS, and a display element layer DP-ED. The display element layer DP-ED includes a pixel defining layer PDL, light emitting elements ED-1, ED-2, and ED-3 disposed between portions of the pixel defining layer PDL, and an encapsulation layer TFE disposed over the light emitting elements ED-1, ED-2, and ED-3.

The substrate layer BS may provide a substrate surface on which the display element layers DP-ED are disposed. The base layer BS may be a glass substrate, a metal substrate, a plastic substrate, or the like. However, the embodiment is not limited thereto, and the base layer BS may include an inorganic layer, an organic layer, or a composite material layer.

In an embodiment, the circuit layer DP-CL may be disposed on the base layer BS, and may include a transistor (not shown). The transistors (not shown) may each include a control electrode, an input electrode, and an output electrode. For example, the circuit layer DP-CL may include switching transistors and driving transistors for driving the light emitting elements ED-1, ED-2, and ED-3 of the display element layer DP-ED.

Each of the light emitting elements ED-1, ED-2, and ED-3 may have a structure of the light emitting element ED according to the embodiment in fig. 3 to 7, which will be described later. Each of the light emitting elements ED-1, ED-2, and ED-3 may include a first electrode EL1, a hole transport region HTR, light emitting layers EML-R, EML-G and EML-B, an electron transport region ETR, and a second electrode EL2.

Fig. 2 illustrates a case where the light emitting layers EML-R, EML-G and EML-B of the light emitting elements ED-1, ED-2 and ED-3 are disposed in the opening OH defined in the pixel defining layer PDL, and the hole transporting region HTR, the electron transporting region ETR and the second electrode EL2 are each provided as a common layer for all the light emitting elements ED-1, ED-2 and ED-3. However, the embodiment is not limited thereto. Although not shown in fig. 2, in an embodiment, the hole transport region HTR and the electron transport region ETR may each be provided by patterning within an opening OH defined in the pixel defining layer PDL. For example, in an embodiment, the hole transport regions HTR, the light emitting layers EML-R, EML-G and EML-B, and the electron transport regions ETR of the light emitting elements ED-1, ED-2, and ED-3 may each be provided by patterning via an inkjet printing process.

The encapsulation layer TFE may cover the light emitting elements ED-1, ED-2 and ED-3. The encapsulation layer TFE may encapsulate the display element layer DP-ED. The encapsulation layer TFE may be a thin film encapsulation layer. The encapsulation layer TFE may be single or multilayer. The encapsulation layer TFE may include at least one insulating layer. The encapsulation layer TFE according to embodiments may include at least one inorganic film (hereinafter, inorganic encapsulation film). In embodiments, the encapsulation layer TFE may include at least one organic film (hereinafter, organic encapsulation film) and at least one inorganic encapsulation film.

The inorganic encapsulation film may protect the display element layer DP-ED from moisture and/or oxygen, and the organic encapsulation film may protect the display device layer DP-ED from foreign substances such as dust particles. The inorganic encapsulation film may include silicon nitride, silicon oxynitride, silicon oxide, titanium oxide, aluminum oxide, or the like, but the embodiment is not limited thereto. The organic encapsulation film may include an acrylic-based compound, an epoxy-based compound, or the like. The organic encapsulation film may include a photopolymerizable organic material, but the embodiment is not limited thereto.

The encapsulation layer TFE may be disposed on the second electrode EL2 and may be disposed to fill the opening OH.

Referring to fig. 1 and 2, the display device DD may include a non-light emitting region NPXA and light emitting regions PXA-R, PXA-G and PXA-B. The light emitting regions PXA-R, PXA-G and PXA-B may each be a region in which light generated by the respective light emitting elements ED-1, ED-2 and ED-3 is emitted. The light emitting areas PXA-R, PXA-G and PXA-B can be spaced apart from each other in plan view.

The light emitting areas PXA-R, PXA-G and PXA-B can each be an area separated by a pixel defining layer PDL. The non-light emitting region NPXA may be a region between adjacent light emitting regions PXA-B, PXA-G and PXA-R, and may correspond to a pixel defining layer PDL. For example, in an embodiment, the light emitting regions PXA-B, PXA-G and PXA-R may each correspond to a pixel. The pixel defining layer PDL may separate the light emitting elements ED-1, ED-2 and ED-3. The light emitting layers EML-R, EML-G and EML-B of the light emitting elements ED-1, ED-2 and ED-3 may be disposed in the opening OH defined in the pixel defining layer PDL and thus separated from each other.

Depending on the color of the light generated by the light emitting elements ED-1, ED-2, and ED-3, the light emitting areas PXA-R, PXA-G and PXA-G may be arranged in groups. In the display device DD according to the embodiment illustrated in fig. 1 and 2, three light emitting regions PXA-R, PXA-G and PXA-B that emit red light, green light and blue light, respectively, are illustrated as examples. For example, the display device DD according to the embodiment may include red, green, and blue light emitting regions PXA-R, PXA-G, and PXA-B that are distinguished from one another.

In the display device DD according to the embodiment, the light emitting elements ED-1, ED-2 and ED-3 may emit light having different wavelength ranges from each other. For example, in an embodiment, the display device DD may include a first light emitting element ED-1 that emits red light, a second light emitting element ED-2 that emits green light, and a third light emitting element ED-3 that emits blue light. For example, the red, green and blue light emitting regions PXA-R, PXA-G and PXA-B of the display device DD may correspond to the first, second and third light emitting elements ED-1, ED-2 and ED-3, respectively.

However, the embodiment is not limited thereto, and the first to third light emitting elements ED-1, ED-2, and ED-3 may emit light in the same wavelength range, or at least one of the first to third light emitting elements ED-1, ED-2, or ED-3 may emit light in different wavelength ranges. For example, the first to third light emitting elements ED-1, ED-2 and ED-3 may all emit blue light.

The light emitting areas PXA-R, PXA-G and PXA-B in the display device DD according to the embodiment may be arranged in a stripe configuration. Referring to fig. 1, the red, green, and blue light emitting regions PXA-R, PXA-G, and PXA-B may be each aligned along a second direction axis DR 2. In another embodiment, the light emitting regions may be alternately arranged along the first direction axis DR1 in the order of the red light emitting regions PXA-R, the green light emitting regions PXA-G, and the blue light emitting regions PXA-B.

Fig. 1 and 2 illustrate that the areas of the light emitting areas PXA-R, PXA-G and PXA-B are similar, but the embodiment is not limited thereto. Accordingly, the areas of the light emitting regions PXA-R, PXA-G and PXA-B may be different from each other according to the wavelength range of the emitted light. The areas of the light emitting areas PXA-R, PXA-G and PXA-B may be areas in a plan view defined by the first and second direction axes DR1 and DR 2.

The arrangement form of the light emitting regions PXA-R, PXA-G and PXA-B is not limited to the arrangement form illustrated in fig. 1, and the order in which the red light emitting regions PXA-R, the green light emitting regions PXA-G and the blue light emitting regions PXA-B are arranged may be provided in various combinations according to the display quality characteristics required for the display device DD. For example, the arrangement of the light emitting areas PXA-R, PXA-G and PXA-B may be PENTILE

Configuration or Diamond Pixel ^TM And (5) configuration.

In embodiments, the areas of the light emitting regions PXA-R, PXA-G and PXA-B may be different from each other in size. For example, in an embodiment, the area of the green light emitting region PXA-G may be smaller than that of the blue light emitting region PXA-B, but the embodiment is not limited thereto.

Hereinafter, fig. 3 to 7 are schematic cross-sectional views illustrating a light emitting element according to an embodiment. Each of the light emitting elements ED according to the embodiment may include a first electrode, a second electrode EL2 facing the first electrode EL1, and at least one functional layer disposed between the first electrode EL1 and the second electrode EL2. The light emitting element ED according to the embodiment may include an amine compound according to the embodiment, which will be described later, in at least one functional layer.

The light emitting element ED may include a hole transport region HTR, an emission layer EML, an electron transport region ETR, and the like, which are stacked in order as at least one functional layer. Referring to fig. 3, the light emitting element ED according to the embodiment may include a first electrode EL1, a hole transport region HTR, a light emitting layer EML, an electron transport region ETR, and a second electrode EL2 stacked in this order.

In comparison with fig. 3, fig. 4 is a schematic cross-sectional view of a light emitting element ED according to an embodiment, wherein the hole transport region HTR includes a hole injection layer HIL and a hole transport layer HTL, and the electron transport region ETR includes an electron injection layer EIL and an electron transport layer ETL. In comparison with fig. 3, fig. 5 is a schematic cross-sectional view of a light emitting element ED according to an embodiment, wherein the hole transport region HTR includes a hole injection layer HIL, a hole transport layer HTL, and an electron blocking layer EBL, and the electron transport region ETR includes an electron injection layer EIL, an electron transport layer ETL, and a hole blocking layer HBL. In comparison with fig. 4, fig. 6 is a schematic cross-sectional view of a light-emitting element ED according to an embodiment, which comprises a cover layer CPL provided on the second electrode EL2. Fig. 7 is a schematic cross-sectional view of a light emitting element ED according to an embodiment, compared to fig. 4, in which the hole transport region HTR includes hole transport layers HTL1 and HTL2.

The light emitting element ED according to the embodiment may include an amine compound according to the embodiment, which will be described later, in the hole transport region HTR. In the light emitting element ED according to the embodiment, at least one of the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL in the hole transport region HTR may contain the amine compound according to the embodiment, or at least one of the first hole transport layer HTL1 and the second hole transport layer HTL2 may contain the amine compound according to the embodiment.

In the light emitting element ED according to the embodiment, the first electrode EL1 has conductivity. The first electrode EL1 may be formed of a metal material, a metal alloy, or a conductive compound. The first electrode EL1 may be an anode or a cathode. However, the embodiment is not limited thereto. For example, the first electrode EL1 may be a pixel electrode. The first electrode EL1 may be a transmissive electrode, a transflective electrode, or a reflective electrode. The first electrode EL1 may include at least one of Ag, mg, cu, al, pt, pd, au, ni, nd, ir, cr, li, ca, liF, mo, ti, W, in, sn, zn, an oxide thereof, a compound thereof, and a mixture thereof.

When the first electrode EL1 is a transmissive electrode, the first electrode EL1 may include a transparent metal oxide, such as Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), zinc oxide (ZnO), or Indium Tin Zinc Oxide (ITZO). When the first electrode EL1 is a transflective electrode or a reflective electrode, the first electrode EL1 may contain Ag, mg, cu, al, pt, pd, au, ni, nd, ir, cr, li, ca, liF/Ca (a stacked structure of LiF and Ca), liF/Al (a stacked structure of LiF and Al), mo, ti, W, a compound thereof, or a mixture thereof (e.g., a mixture of Ag and Mg). In another embodiment, the first electrode EL1 may have a multilayer structure including a reflective film or a transflective film formed of the above materials, and a transmissive conductive film formed of ITO, IZO, znO, ITZO or the like. For example, the first electrode EL1 may include a three-layer structure of ITO/Ag/ITO. However, the embodiment is not limited thereto. The first electrode EL1 may contain the above-described metal material, a combination of two or more metal materials selected from the above-described metal materials, or an oxide of the above-described metal material. The first electrode EL1 may have about

To about->

Is a thickness of (c). For example, the first electrode EL1 may have about +.>

To about->

Is a thickness of (c).

A hole transport region HTR is provided on the first electrode EL 1. The hole transport region HTR may be a single layer formed of a single material, a single layer formed of different materials, or a structure having a plurality of layers formed of different materials.

The hole transport region HTR may include at least one of a hole injection layer HIL, a hole transport layer HTL, a buffer layer (not shown), and an electron blocking layer EBL. In an embodiment, the hole transport region HTR may have a structure in which a hole injection layer HIL, a first hole transport layer HTL1, and a second hole transport layer HTL2 are stacked in this order.

For example, the hole transport region HTR may have a structure of a single layer of the hole injection layer HIL or the hole transport layer HTL, or may have a structure of a single layer formed of a hole injection material and a hole transport material. In the embodiment, the hole transport region HTR may have a structure of a single layer formed of different materials, or may have a structure in which a hole injection layer HIL/hole transport layer HTL, a hole injection layer HIL/hole transport layer HTL/buffer layer (not shown), a hole injection layer HIL/buffer layer (not shown), or a hole transport layer HTL/buffer layer (not shown) are stacked in their respective prescribed order from the first electrode EL1, but the embodiment is not limited thereto.

The hole transport region HTR may have, for example, about

To about->

Is a thickness of (c). The hole transport region HTR may be formed using various methods, such as a vacuum deposition method, a spin coating method, a casting method, a Langmuir-Blodgett (LB) method, an inkjet printing method, a laser printing method, and a Laser Induced Thermal Imaging (LITI) method.

The light emitting element ED according to the embodiment may include the amine compound according to the embodiment represented by formula 1 in the hole transport region HTR. In the light emitting element ED according to the embodiment, the hole transport layer HTL may include the amine compound according to the embodiment represented by formula 1, and in the light emitting element ED according to the embodiment, the second hole transport layer HTL2 may include the amine compound according to the embodiment represented by formula 1.

[ 1]

In formula 1, R ₁ And R is ₂ R and/or R of (C) ₃ And R is ₄ May be bonded to the group represented by formula 2 to form a ring.

[ 2]

The amine compound according to an embodiment may have at least two naphthyl groups and may include a dibenzo-heterocyclic (dibenzo-heterocyclic) group as a linker moiety between at least one of the naphthyl groups and the nitrogen atom of the amine moiety. The two naphthyl groups of the amine compound according to embodiments may be bonded to an aryl group or a dibenzocyclopentadiene moiety, respectively, at para positions relative to the nitrogen atom of the amine moiety.

In formula 1, ar ₁ May be a substituted or unsubstituted aryl group having from 6 to 40 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having from 5 to 40 ring-forming carbon atoms. In embodiments, ar ₁ Phenanthryl groups having high planarity can be excluded. In embodiments, ar ₁ May be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzothiophene group, or a substituted or unsubstituted dibenzofuran group. However, the embodiment is not limited thereto.

In formula 1, R ₁ To R ₄ Can each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted carbon atom having 1 to 20 carbon atomsAn alkyl group, a substituted or unsubstituted aryl group having 6 to 40 ring-forming carbon atoms, or a single bond forming a ring by bonding with the group represented by formula 2. R is R ₁ And R is ₂ R and/or R of (C) ₃ And R is ₄ May be bonded to the group represented by formula 2 to form a ring of dibenzocyclopentadiene.

In formula 2, X may be O, S, N (R ₁₀ ) Or C (R) ₁₁ )(R ₁₂ ) And a and b each represent R in formula 1 ₁ To R ₄ One of the keys. For example, a and b may be equal to R ₁ And R is ₂ To form a ring, or a and b may be combined with R ₃ And R is ₄ Bonding to form a ring. By R ₁ And R is ₂ R and/or R of (C) ₃ And R is ₄ The ring formed by bonding the pairs of the compounds represented by formula 2 may be dibenzofuran derivatives, dibenzothiophene derivatives, carbazole derivatives or fluorene derivatives.

In formula 1 and formula 2, R ₅ To R ₁₂ May each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 40 ring-forming carbon atoms. In

formulas

1 and 2, a and b may each independently be an integer of 0 to 2, c and d may each independently be an integer of 0 to 7, and e may be an integer of 0 to 4.

When a to e are each 2 or more than 2, R ₅ To R ₉ The multiple groups of (a) may be the same or different from each other. For example, when a is 2, two R ₅ The groups may be the same or different from each other. The description can be similarly applied to R ₆ To R ₉ Each of which is formed by a pair of metal plates.

In embodiments, in the amine compound represented by formula 1 and the group represented by formula 2, R ₁ To R ₉ May be a deuterium atom or a substituent comprising a deuterium atom; and/or Ar ₁ May be a substituent comprising a deuterium atom. For example, an amine compound according to an embodiment may include at least one deuterium atom as a substituent.

In an embodiment, the amine compound represented by formula 1 may be a monoamine compound. The amine compound according to an embodiment may not include an amine group as a substituent.

In an embodiment, the amine compound represented by formula 1 may be represented by any one of formulas 1-1 to 1-3.

[ 1-1]

[ 1-2]

[ 1-3]

In the formulae 1 to 3, X ₁ And X ₂ Can each independently be O, S, N (R ₁₀ ) Or C (R) ₁₁ )(R ₁₂ ) The method comprises the steps of carrying out a first treatment on the surface of the e1 and e2 may each independently be an integer from 0 to 4; r is as follows ₉₁ And R is ₉₂ May each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 40 ring-forming carbon atoms.

In the formulae 1 to 3, X ₁ And X ₂ May be the same or different from each other. For example, in an embodiment, X ₁ And X ₂ Can be identical and X ₁ And X ₂ Both may be O or S. In the formulae 1-1 to 1-3, ar ₁ 、X、R ₁ 、R ₂ 、R ₅ To R ₁₂ And a to e may be the same as those described in

formulas

1 and 2.

In an embodiment, the group represented by formula 2 may be represented by any one of formulas 2-1 to 2-5.

In formulae 2-1 to 2-5, a and b may each represent R of formula 1 ₁ To R ₄ Any one of the keys. In the formulae 2-1 to 2-5, R ₉ E, a and b are the same as defined in formula 2.

The amine compound according to the embodiment represented by formula 1 may be selected from compound group 1. The hole transport region HTR of the light emitting element ED according to the embodiment may include at least one of the amine compounds in the compound group 1. In compound group 1, D represents a deuterium atom.

[ Compound group 1]

The amine compound according to the embodiment represented by formula 1 and formula 2 may include at least one dibenzo-dicyclopentadiene moiety substituted with a naphthyl group. In the amine compound according to the embodiment, the dibenzocyclopentadiene moiety may be protected by a naphthyl group having excellent heat resistance and charging resistance to prevent deterioration, and thus the stability of the amine compound according to the embodiment may be improved. The lifetime of the light emitting element according to the embodiment including the amine compound according to the embodiment may also be improved. Since the amine compound according to the embodiment may contain at least one dibenzo-dicyclopentadiene moiety having a naphthyl group as a substituent, the symmetry of the molecule is reduced and thus the crystallinity is suppressed, thereby improving hole transport properties when used in a light emitting element. Therefore, the light-emitting efficiency of the light-emitting element according to the embodiment including the amine compound according to the embodiment can also be improved.

When the light emitting element ED according to the embodiment includes the hole transport layers HTL1 and HTL2, the second hole transport layer HTL2 adjacent to the light emitting layer EML may contain the amine compound of the above-described embodiment. The first hole transport layer HTL1 disposed under the second hole transport layer HTL2 and adjacent to the first electrode EL1 may include an amine derivative compound represented by formula 3.

[ 3]

In formula 3, L _a May be a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms. In formula 3, R _a1 To R _a4 May each independently be a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, or may be bonded to an adjacent group to form a ring.

For example, L _a May be a direct bond or a substituted or unsubstituted phenylene group. For example, R _a1 May be a substituted or unsubstituted phenyl group. However, the embodiment is not limited thereto.

In the amine derivative compound represented by formula 3, R _a2 May be an aryl group or a heteroaryl group. Example(s)For example, R _a2 May be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene group.

The amine derivative compound represented by formula 3 may be represented by compound HT1. In an embodiment, the first hole transport layer HTL1 may include a compound HT1.

The light emitting element ED according to the embodiment may further include a material for a hole transport region in the hole transport region HTR in addition to the amine compound according to the embodiment and the amine derivative compound represented by formula 3.

The hole transport region HTR may include a compound represented by formula H-1.

[ H-1]

In formula H-1, L ₁ And L ₂ May each independently be a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms. In formula H-1, a and b may each independently be an integer of 0 to 10. When a or b is 2 or greater than 2, a plurality of L ₁ Radicals and a plurality of L ₂ The groups may each independently be a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms.

In formula H-1, ar ₁ And Ar is a group ₂ May each independently be a substituted or unsubstituted aryl group having from 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring-forming carbon atoms. In formula H-1, ar ₃ May be a substituted or unsubstituted aryl group having from 6 to 30 ring-forming carbon atoms.

In an embodiment, the compound represented by formula H-1 may be a monoamine compound. In another embodiment, the compound represented by the formula H-1 may be a diamine compound in which Ar ₁ To Ar ₃ Comprises an amine group as a substituent. In yet another embodiment, the compound represented by formula H-1 may be wherein Ar ₁ And Ar is a group ₂ A carbazole-based compound including a substituted or unsubstituted carbazole group, or may be wherein Ar ₁ And Ar is a group ₂ A fluorene-based compound comprising a substituted or unsubstituted fluorene group.

The compound represented by the formula H-1 may be any one selected from the group of compounds H. However, the compounds listed in the compound group H are only examples, and the compound represented by the formula H-1 is not limited to the compound group H.

[ Compound group H ]

The hole-transporting region HTR may comprise a phthalocyanine compound (e.g., copper phthalocyanine), N1' - ([ 1,1' -biphenyl ] -4,4' -diyl) bis (N1-phenyl-N4, N4-di-m-tolylbenzene-1, 4-diamine) (DNTPD), 4',4"- [ tris (3-methylphenyl) phenylamino ] triphenylamine (m-MTDATA), 4',4" -tris (N, N-diphenylamino) triphenylamine (TDATA), 4',4 "-tris [ N- (2-naphthyl) -N-phenylamino ] -triphenylamine (2-TNATA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenesulfonate) (PEDOT/PSS), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA), polyaniline/camphorsulfonic acid (PANI/CSA), polyaniline/poly (4-styrenesulfonate) (PANI/DBSA), N ' -bis (naphthalene-l-yl) -N, N ' -diphenyl-anilide (npf) or tris [ 4-iodophenyl ] -triphenylamine (npf-4-isopropyl-containing) polyethere (npf ); 2',3' -h ] quinoxaline-2, 3,6,7,10, 11-hexacarbonitrile (HAT-CN), and the like.

The hole transport region HTR may include carbazole derivatives (e.g., N-phenylcarbazole and polyvinylcarbazole), fluorene-based derivatives, N ' -bis (3-methylphenyl) -N, N ' -diphenyl- [1,1' -biphenyl ] -4,4' -diamine (TPD), triphenylamine derivatives (e.g., 4',4 "-tris (N-carbazolyl) triphenylamine (TCTA)), N ' -bis (naphthalen-l-yl) -N, N ' -diphenyl-benzidine (NPB), 4' -cyclohexylidenebis [ N, N-bis (4-methylphenyl) aniline ] (TAPC), 4' -bis [ N, N ' - (3-tolyl) amino ] -3,3' -dimethylbiphenyl (HMTPD), 1, 3-bis (N-carbazolyl) benzene (mCP), and the like.

The hole transport region HTR may comprise 9- (4-tert-butylphenyl) -3, 6-bis (triphenylsilyl) -9H-carbazole (CzSi), 9-phenyl-9H-3, 9' -dicarbazole (CCP), 1, 3-bis (1, 8-dimethyl-9H-carbazol-9-yl) benzene (mDCP), or the like.

The hole transport region HTR may include the above-described compound of the hole transport region in at least one of the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL.

The hole transport region HTR may have about

To about->

Is a thickness of (c). For example, the hole transport region HTR may have about +.>

To about->

Is a thickness of (c). When the hole transport region HTR includes the hole injection layer HIL, the hole injection layer HIL may have, for example, about +.>

To about->

Is a thickness of (c). When the hole transport region HTR includes a hole transport layer HTL, the hole transport layer HTL may have about +>

To about->

Is a thickness of (c). When the hole transport region HTR includes an electron blocking layer EBL, the electron blocking layer EBL may have about +.>

To about->

Is a thickness of (c). When the thicknesses of the hole transport region HTR, the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL satisfy the above-described ranges, satisfactory hole transport properties can be achieved without a significant increase in driving voltage.

In addition to the above-described materials, the hole transport region HTR may further include a charge generation material to increase conductivity. The charge generating material may be uniformly or non-uniformly dispersed in the hole transport region HTR. The charge generating material may be, for example, a p-dopant. The p-dopant may include at least one of a metal halide compound, a quinone derivative, a metal oxide, and a cyano group-containing compound, but the embodiment is not limited thereto. For example, the p-type dopant may include halogenated metal compounds such as CuI and RbI, quinone derivatives such as Tetracyanoquinodimethane (TCNQ) and 2,3,5, 6-tetrafluoro-7, 7', 8' -tetracyanoquinodimethane (F4-TCNQ), metal oxides such as tungsten oxide and molybdenum oxide, cyano group-containing compounds such as dipeazino [2,3-F:2',3' -h ] quinoxaline-2, 3,6,7,10, 11-hexacarbonitrile (HAT-CN), and 4- [ [2, 3-bis [ cyano- (4-cyano-2, 3,5, 6-tetrafluorophenyl) methylene ] cyclopropyl ] -cyanomethyl ] -2,3,5, 6-tetrafluorobenzonitrile (NDP 9), and the like, but the embodiment is not limited thereto.

As described above, the hole transport region HTR may further include at least one of a buffer layer (not shown) and an electron blocking layer EBL in addition to the hole injection layer HIL and the hole transport layer HTL. The buffer layer (not shown) may compensate for the resonance distance according to the wavelength of light emitted from the light emitting layer EML and may increase the light emitting efficiency. As a material contained in the buffer layer (not shown), a material that can be contained in the hole transport region HTR can be used. The electron blocking layer EBL may prevent electrons from being injected from the electron transport region ETR into the hole transport region HTR.

The light emitting layer EML is provided on the hole transport region HTR. The light emitting layer EML may have, for example, about

To about

Is a thickness of (c). For example, the light emitting layer EML may have about +.>

To about->

Is a thickness of (c). The light emitting layer EML may be a single layer formed of a single material, a single layer formed of different materials, or a structure having a plurality of layers formed of different materials.

In the light emitting element ED according to the embodiment, the light emitting layer EML may emit blue light. The light emitting element ED according to the embodiment may include the amine compound according to the embodiment described above in the hole transport region HTR to exhibit high light emitting efficiency and long service life characteristics in the blue light emitting region. However, the embodiment is not limited thereto.

In the light emitting element ED according to the embodiment, the light emitting layer EML may include an anthracene derivative, a pyrene derivative, a fluoranthene derivative,

Derivatives, dihydrobenzanthracene derivatives or benzophenanthrene derivatives. For example, the light emitting layer EML may comprise an anthracene derivativeBiological or pyrene derivatives.

In the light emitting element ED according to the embodiment illustrated in fig. 3 to 7, the light emitting layer EML may include a host and a dopant, and the light emitting layer EML may include a compound represented by formula E-1. The compound represented by formula E-1 can be used as a fluorescent host material.

[ E-1]

In formula E-1, R ₃₁ To R ₄₀ May each independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, or may be bonded to an adjacent group to form a ring. For example, R ₃₁ To R ₄₀ May be bonded to adjacent groups to form saturated hydrocarbon rings, unsaturated hydrocarbon rings, saturated heterocyclic rings, or unsaturated heterocyclic rings.

In formula E-1, c and d may each independently be an integer of 0 to 5.

The compound represented by the formula E-1 may be any one selected from the group consisting of the compounds E1 to E19.

In an embodiment, the light emitting layer EML may include a compound represented by formula E-2a or formula E-2 b. The compound represented by formula E-2a or formula E-2b may be used as a phosphorescent host material.

[ E-2a ]

In formula E-2a, a may be an integer from 0 to 10, and La may be a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms. When a is 2 or greater than 2, the plurality of La groups may each independently be a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms.

In formula E-2a, A ₁ To A ₅ Can each independently be N or C (R _i ). In formula E-2a, R _a To R _i May each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted amine group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, or may be bonded to an adjacent group to form a ring. For example, R _a To R _i May be bonded to an adjacent group to form a hydrocarbon ring or a heterocyclic ring containing N, O, S or the like as a ring-forming atom.

In formula E-2a, A ₁ To A ₅ Two or three of (a) may be N, and A ₁ To A ₅ The remainder of (C) may be C (R _i )。

[ E-2b ]

In formula E-2b, cbz1 and Cbz2 may each independently be absentA substituted carbazole group, or a carbazole group substituted with an aryl group having 6 to 30 ring-forming carbon atoms. In formula E-2b, L _b May be a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms. In formula E-2b, b may be an integer from 0 to 10. When b is 2 or greater than 2, a plurality of L _b The groups may each independently be a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms.

The compound represented by the formula E-2a or the formula E-2b may be any one selected from the group of compounds E-2. However, the compounds listed in the compound group E-2 are only examples, and the compounds represented by the formula E-2a or the formula E-2b are not limited to the compound group E-2.

[ Compound group E-2]

The light emitting layer EML may further include a material of the related art as a host material. For example, the light emitting layer EML may include bis (4- (9H-carbazol-9-yl) phenyl) diphenylsilane (BCPDS), (4- (1- (4- (diphenylamino) phenyl) cyclohexyl) phenyl) diphenyl-phosphine oxide (popppa), bis [2- (diphenylphosphino) phenyl)]Ether oxide (DPEPO), 4 '-bis (N-carbazolyl) -1,1' -biphenyl (CBP), 1, 3-bis (carbazol-9-yl) benzene (mCP), 2, 8-bis (diphenylphosphoryl) dibenzo [ b, d ]]Furan (PPF), 4' -tris (carbazol-9-yl) -triphenylamine (TCTA) and 1,3, 5-tris (1-phenyl-1H-benzo [ d ]]At least one of imidazol-2-yl) benzene (TPBi) as a host material. However, the embodiment is not limited thereto. For example, tris (8-hydroxyquinolinato) aluminum (Alq ₃ ) 9, 10-di (naphthalen-2-yl) Anthracene (ADN), 2-tert-butyl-9, 10-di (naphthalen-2-yl) anthracene (TBADN), diphenylethyleneAlkenyl arylene (DSA), 4 '-bis (9-carbazolyl) -2,2' -dimethyl-biphenyl (CDBP), 2-methyl-9, 10-bis (naphthalen-2-yl) anthracene (MADN), hexaphenyl cyclotriphosphazene (CP 1), 1, 4-bis (triphenylsilyl) benzene (UGH 2), hexaphenyl cyclotrisiloxane (DPSiO ₃ ) Octaphenyl cyclotetrasiloxane (DPSiO) ₄ ) Etc. may be used as host materials.

The light emitting layer EML may include a compound represented by formula M-a or formula M-b. The compounds represented by formula M-a or formula M-b may be used as phosphorescent dopant materials. In embodiments, compounds represented by formula M-a or formula M-b may be used as auxiliary dopant materials.

[ M-a ]

In formula M-a, Y ₁ To Y ₄ And Z ₁ To Z ₄ Can each independently be C (R ₁ ) Or N, and R ₁ To R ₄ May each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted amine group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, or may be bonded to an adjacent group to form a ring. In formula M-a, M may be 0 or 1, and n may be 2 or 3. In formula M-a, n may be 3 when M is 0, and n may be 2 when M is 1.

The compounds represented by formula M-a may be used as phosphorescent dopant materials.

The compound represented by the formula M-a may be any one selected from the group consisting of the compounds M-a1 to M-a25. However, the compounds M-a1 to M-a25 are merely examples, and the compounds represented by the formula M-a are not limited to the compounds M-a1 to M-a25.

The compounds M-a1 and M-a2 may be used as red dopant materials, and the compounds M-a3 to M-a7 may be used as green dopant materials.

[ M-b ]

In formula M-b, Q ₁ To Q ₄ May each independently be C or N, and C1 to C4 may each independently be a substituted or unsubstituted hydrocarbon ring having 5 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic ring having 2 to 30 ring-forming carbon atoms. In formula M-b, L ₂₁ To L ₂₄ Can be independently a direct bond, an-o-, an-s-, a-or a-c,

A substituted or unsubstituted divalent alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms, and e1 to e4 may each independently be 0 or 1. In the formula M-b, R ₃₁ To R ₃₉ May each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, or may be bonded to an adjacent group Groups to form a ring, and d1 to d4 may each independently be an integer of 0 to 4. Can represent bonding sites with adjacent atoms.

The compound represented by formula M-b may be used as a blue phosphorescent dopant or a green phosphorescent dopant. In an embodiment, the compound represented by formula M-b may be further included in the emission layer EML as an auxiliary dopant.

The compound represented by the formula M-b may be any one selected from the group consisting of the compounds M-b-1 to M-b-11. However, the compounds M-b-1 to M-b-11 are merely examples, and the compounds represented by the formula M-b are not limited to the compounds M-b-1 to M-b-11.

R, R among the compounds M-b-9 and M-b-11 ₃₈ And R is ₃₉ May each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.

The light emitting layer EML may include a compound represented by any one of formulas F-a to F-c. The compounds represented by formulas F-a to F-c may be used as fluorescent dopant materials.

[ F-a ]

In formula F-a, R _a To R _j Can be each independently selected from the group consisting of ₁ Ar ₂ The indicated groups are substituted. R is R _a To R _j Is not represented by NAr ₁ Ar ₂ The remainder of the substituents represented by the groups may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amineA group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. At the following: -NAr ₁ Ar ₂ Ar in the group represented by ₁ And Ar is a group ₂ May each independently be a substituted or unsubstituted aryl group having from 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring-forming carbon atoms. For example, ar ₁ And Ar is a group ₂ May be a heteroaryl group containing O or S as a ring-forming atom. Can represent bonding sites with adjacent atoms.

[ F-b ]

In formula F-b, R _a And R is _b May each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, or may be bonded to an adjacent group to form a ring. In formula F-b, ar ₁ To Ar ₄ May each independently be a substituted or unsubstituted aryl group having from 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring-forming carbon atoms.

In formula F-b, U and V may each independently be a substituted or unsubstituted hydrocarbon ring having 5 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic ring having 2 to 30 ring-forming carbon atoms.

In formula F-b, the number of rings represented by U and V may each independently be 0 or 1. For example, in formula F-b, when the number of U or V is 1, a condensed ring may exist at a portion designated as U or V, and when the number of U or V is 0, a condensed ring may exist at a portion designated as U or V. When the number of U is 0 and the number of V is 1, or when the number of U is 1 and the number of V is 0, the condensed ring having a fluorene core of formula F-b may be a cyclic compound having four rings. When both the number of U and the number of V are 0, the fused ring having a fluorene core of formula F-b may be a cyclic compound having three rings. When both the number of U and the number of V are 1, the fused ring having a fluorene core of formula F-b may be a cyclic compound having five rings.

[ F-c ]

In formula F-c, A ₁ And A ₂ Can each independently be O, S, se or N (R _m ) And R is _m May be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. In formula F-c, R ₁ To R ₁₁ May each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted oxygen group, a substituted or unsubstituted sulfur group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, or may be bonded to an adjacent group to form a ring.

In formula F-c, A ₁ And A ₂ Substituents that may each independently bond to adjacent rings to form fused rings. For example, when A ₁ And A ₂ Each independently is N (R) _m ) When A is ₁ Can be bonded to R ₄ Or R is ₅ To form a ring. For example, A ₂ Can be bonded to R ₇ Or R is ₈ To form a ring.

In embodiments, the light emitting layer EML may include dopant materials of related art, such as styryl derivatives (e.g., 1, 4-bis [2- (3-N-ethylcarbazolyl) vinyl ] benzene (BCzVB), 4- (di-p-tolylamino) -4' - [ (di-p-tolylamino) styryl ] stilbene (DPAVB), N- (4- ((E) -2- (6- ((E) -4- (diphenylamino) styryl) naphthalene-2-yl) vinyl) phenyl) -N-phenylaniline (N-BDAVBi), 4' -bis [2- (4- (N, N-diphenylamino) phenyl) vinyl ] biphenyl (DPAVBi)), perylene and derivatives thereof (e.g., 2,5,8, 11-tetra-t-butylperylene (TBP)), pyrene and derivatives thereof (e.g., 1' -dipyrene, 1, 4-dipyrene-p-enyl, 1, 4-bis (N, N-diphenylamino)), and the like.

In embodiments, when a plurality of light emitting layers EML are included, at least one light emitting layer EML may include a phosphorescent dopant material of the related art. For example, the phosphorescent dopant material may include a metal complex including iridium (Ir), platinum (Pt), osmium (Os), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), or thulium (Tm). For example, bis (4, 6-difluorophenylpyridyl-N, C2') iridium (III) (FIrpic), bis (2, 4-difluorophenylpyridyl) -tetrakis (1-pyrazolyl) borate iridium (III) (Fir 6), or platinum octaethylporphyrin (PtOEP) may be used as phosphorescent dopant materials. However, the embodiment is not limited thereto.

In an embodiment, the light emitting layer EML may include a hole transporting host and an electron transporting host. The emission layer EML may include an auxiliary dopant and an emission dopant. The auxiliary dopant may include a phosphorescent dopant material or a thermally activated delayed fluorescence dopant material. For example, in an embodiment, the light emitting layer EML may include a hole transporting host, an electron transporting host, an auxiliary dopant, and a light emitting dopant.

In the light emitting layer EML, an exciplex may be formed of a hole transporting host and an electron transporting host. The triplet energy of the exciplex formed by the hole-transporting host and the electron-transporting host may correspond to a separation T1 between the Lowest Unoccupied Molecular Orbital (LUMO) energy level of the electron-transporting host and the Highest Occupied Molecular Orbital (HOMO) energy level of the hole-transporting host.

In embodiments, the triplet energy (T1) of the exciplex formed from the hole transporting host and the electron transporting host may be from about 2.4eV to about 3.0eV. The triplet energy level of the exciplex may be a value less than the energy gap of each host material. For example, the exciplex may have a triplet energy level equal to or less than about 3.0eV, which may be an energy gap between the hole transporting host and the electron transporting host.

The at least one light emitting layer EML may comprise a quantum dot material. The quantum dots may be selected from group II-VI compounds, group III-VI compounds, group I-III-VI compounds, group III-V compounds, group III-II-V compounds, group IV-VI compounds, group IV elements, group IV compounds, and combinations thereof.

The group II-VI compound may be selected from: a binary compound selected from the group consisting of CdSe, cdTe, cdS, znS, znSe, znTe, znO, hgS, hgSe, hgTe, mgSe, mgS and mixtures thereof; a ternary compound selected from the group consisting of CdSeS, cdSeTe, cdSTe, znSeS, znSeTe, znSTe, hgSeS, hgSeTe, hgSTe, cdZnS, cdZnSe, cdZnTe, cdHgS, cdHgSe, cdHgTe, hgZnS, hgZnSe, hgZnTe, mgZnSe, mgZnS and mixtures thereof; a quaternary compound selected from the group consisting of CdZnSeS, cdZnSeTe, cdZnSTe, cdHgSeS, cdHgSeTe, cdHgSTe, hgZnSeS, hgZnSeTe, hgZnSTe and mixtures thereof; or any combination thereof.

The III-VI compound may be selected from: binary compounds, e.g. In ₂ S ₃ And In ₂ Se ₃ The method comprises the steps of carrying out a first treatment on the surface of the Ternary compounds, e.g. InGaS ₃ And InGaSe ₃ The method comprises the steps of carrying out a first treatment on the surface of the Or any combination thereof.

The group I-III-VI compound may be selected from: a ternary compound selected from the group consisting of AgInS, agInS ₂ 、CuInS、CuInS ₂ 、AgGaS ₂ 、CuGaS ₂ 、CuGaO ₂ 、AgGaO ₂ 、AgAlO ₂ And mixtures thereof; quaternary compounds, e.g. AgInGaS ₂ And CuInGaS ₂ Etc.; or any combination thereof.

The III-V compounds may be selected from: a binary compound selected from the group consisting of GaN, gaP, gaAs, gaSb, alN, alP, alAs, alSb, inN, inP, inAs, inSb and mixtures thereof; a ternary compound selected from the group consisting of GaNP, gaNAs, gaNSb, gaPAs, gaPSb, alNP, alNAs, alNSb, alPAs, alPSb, inGaP, inAlP, inNP, inNAs, inNSb, inPAs, inPSb and mixtures thereof; a quaternary compound selected from the group consisting of GaAlNP, gaAlNAs, gaAlNSb, gaAlPAs, gaAlPSb, gaInNP, gaInNAs, gaInNSb, gaInPAs, gaInPSb, inAlNP, inAlNAs, inAlNSb, inAlPAs, inAlPSb and mixtures thereof; or any combination thereof. The group III-V compound may further comprise a group II metal. For example, inZnP or the like may be selected as the group III-II-V compound.

The IV-VI compounds may be selected from: a binary compound selected from the group consisting of SnS, snSe, snTe, pbS, pbSe, pbTe and mixtures thereof; a ternary compound selected from the group consisting of SnSeS, snSeTe, snSTe, pbSeS, pbSeTe, pbSTe, snPbS, snPbSe, snPbTe and mixtures thereof; a quaternary compound selected from the group consisting of SnPbSSe, snPbSeTe, snPbSTe and mixtures thereof; or any combination thereof. The group IV element may be selected from the group consisting of Si, ge, and mixtures thereof. The group IV compound may be a binary compound selected from the group consisting of SiC, siGe, and mixtures thereof.

The binary, ternary or quaternary compounds may be present in the particles in uniform concentrations or may be present in the particles in partially different concentrations. In embodiments, the quantum dot may have a core/shell structure in which the quantum dot surrounds another quantum dot. Quantum dots having a core/shell structure may have a concentration gradient in which the concentration of elements present in the shell decreases toward the center thereof.

In embodiments, the quantum dot may have a core/shell structure including a core having the nanocrystals described above and a shell surrounding the core. The shell of the quantum dot may serve as a protective layer for maintaining semiconductor characteristics by preventing chemical denaturation of the core, and/or may serve as a charge layer for imparting electrophoretic properties to the quantum dot. The shell may be a single layer or multiple layers. Examples of the shell of the quantum dot may include a metal oxide, a non-metal oxide, a semiconductor compound, or a combination thereof.

Examples of metal oxides or non-metal oxides may include binary compounds (e.g., siO ₂ 、Al ₂ O ₃ 、TiO ₂ 、ZnO、MnO、Mn ₂ O ₃ 、Mn ₃ O ₄ 、CuO、FeO、Fe ₂ O ₃ 、Fe ₃ O ₄ 、CoO、Co ₃ O ₄ And NiO) or ternary compounds (e.g., mgAl ₂ O ₄ 、CoFe ₂ O ₄ 、NiFe ₂ O ₄ And CoMn ₂ O ₄ ) But the embodiment is not limited thereto.

Examples of the semiconductor compound may include CdS, cdSe, cdTe, znS, znSe, znTe, znSeS, znTeS, gaAs, gaP, gaSb, hgS, hgSe, hgTe, inAs, inP, inGaP, inSb, alAs, alP, alSb and the like, but the embodiment is not limited thereto.

The quantum dots may have a full width at half maximum (FWHM) of the emission wavelength spectrum equal to or less than about 45 nm. For example, the quantum dots may have a FWHM of the emission wavelength spectrum equal to or less than about 40 nm. For example, the quantum dots may have a FWHM of the emission wavelength spectrum equal to or less than about 30 nm. Within these ranges, color purity or color reproducibility can be improved. Light emitted through the quantum dots can be emitted in all directions, so that a wide viewing angle characteristic can be improved.

The shape of the quantum dot may be any form used in the related art, without limitation. For example, the quantum dots may have a spherical shape, a pyramidal shape, a multi-armed shape, or a cubic shape, or the quantum dots may be in the form of nanoparticles, nanotubes, nanowires, nanofibers, nanoplates, or the like.

The quantum dots may control the color of the emitted light according to the particle size thereof, and thus, the quantum dots may have various colors of the emitted light, such as blue, red, or green.

In the light emitting element ED according to the embodiment as illustrated in fig. 3 to 7, the electron transport region ETR is provided on the light emitting layer EML. The electron transport region ETR may include at least one of a hole blocking layer HBL, an electron transport layer ETL, and an electron injection layer EIL. However, the embodiment is not limited thereto.

The electron transport region ETR may be a single layer formed of a single material, a single layer formed of different materials, or a structure having a plurality of layers formed of different materials.

For example, the electron transport region ETR may have a structure of an electron injection layer EIL or a single layer of the electron transport layer ETL, or may have a single layer structure formed of an electron injection material and an electron transport material. In other embodiments, the electron transport region ETR may have a structure of a single layer formed of different materials, or may have a structure in which an electron transport layer ETL/an electron injection layer EIL, a hole blocking layer HBL/an electron transport layer ETL/an electron injection layer EIL, or an electron transport layer ETL/a buffer layer (not shown)/an electron injection layer EIL are stacked in their respective prescribed order from the light emitting layer EML, but the embodiments are not limited thereto. The electron transport region ETR may have, for example, about

To about->

Is a thickness of (c).

The electron transport region ETR may be formed by various methods, such as a vacuum deposition method, a spin coating method, a casting method, a langmuir-blodgett (LB) method, an inkjet printing method, a laser printing method, and a Laser Induced Thermal Imaging (LITI) method.

The electron transport region ETR may comprise a compound represented by the formula ET-1.

[ ET-1]

In formula ET-1, X ₁ To X ₃ At least one of which may be N, and X ₁ To X ₃ The remainder of (C) may be C (R _a ) The method comprises the steps of carrying out a first treatment on the surface of the And R is _a May be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. In formula ET-1, ar ₁ To Ar ₃ May each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.

In formula ET-1, a to c may each independently be an integer of 0 to 10. In formula ET-1, L ₁ To L ₃ May each independently be a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms. When a to c are 2 or more than 2, L ₁ To L ₃ Each independently may be a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms.

The electron transport region ETR may comprise an anthracene-based compound. However, the embodiment is not limited thereto, and the electron transport region ETR may include, for example, tris (8-hydroxyquinolinato) aluminum (Alq ₃ ) 1,3, 5-tris [ (3-pyridyl) -benzene-3-yl]Benzene, 2,4, 6-tris (3' - (pyridin-3-yl) biphenyl-3-yl) -1,3, 5-triazine, 2- (4- (N-phenylbenzimidazol-1-yl) phenyl) -9, 10-dinaphthyl anthracene, 1,3, 5-tris (1-phenyl-1H-benzo [ d ]]Imidazol-2-yl) benzene (TPBi), 2, 9-dimethyl-4, 7-diphenyl-1, 10-phenanthroline (BCP), 4, 7-diphenyl-1, 10-phenanthroline (Bphen), 3- (4-diphenyl) -4-phenyl-5-tert-butylphenyl-1, 2, 4-Triazole (TAZ), 4- (naphthalen-1-yl) -3, 5-diphenyl-4H-1, 2, 4-triazole (NTAZ), 2- (4-diphenyl) -5- (4-tert-butylphenyl) -1,3, 4-oxadiazole (tBu-PBD), bis (2-methyl-8-quinolinato-N1, O8) - (1, 1' -biphenyl-4-yl) aluminum (BAlq), bis (benzoquinolin-10-yl) beryllium (Bebq) ₂ ) 9, 10-bis (naphthalen-2-yl) Anthracene (ADN), 1, 3-bis [3, 5-bis (pyridin-3-yl) benzeneBase group]Benzene (BmPyPhB), diphenyl (4- (triphenylsilyl) phenyl) phosphine oxide (TSPO 1) and mixtures thereof.

The electron transport region ETR may include at least one of the compounds ET1 to ET 36.

The electron transport region ETR may comprise a metal halide (e.g., liF, naCl, csF, rbCl, rbI, cuI or KI), a lanthanide metal (e.g., yb), or a co-deposited material of a metal halide and a lanthanide metal. For example, the electron transport region ETR may contain KI: yb, rbI: yb, etc., as the co-deposited material. The electron transport region ETR may contain, for example, li ₂ Metal oxides of O and BaO or lithium 8-hydroxy-quinoline (Liq), but the embodiment is not limited thereto. The electron transport region ETR may also be formed of a mixture material of an electron transport material and an insulating organic metal salt. The organometallic salt can be a material having an energy band gap equal to or greater than about 4 eV. For example, the organometallic salt may include a metal acetate, a metal benzoate, a metal acetoacetate, a metal acetylacetonate, or a metal stearate.

In addition to the above-described materials, the electron transport region ETR may further include at least one of 2, 9-dimethyl-4, 7-diphenyl-1, 10-phenanthroline (BCP), diphenyl (4- (triphenylsilyl) phenyl) phosphine oxide (TSPO 1), and 4, 7-diphenyl-1, 10-phenanthroline (Bphen). However, the embodiment is not limited thereto.

The electron transport region ETR may contain the above-described compound of the electron transport region ETR in at least one of the electron injection layer EIL, the electron transport layer ETL, and the hole blocking layer HBL.

When the electron transport region ETR includes an electron transport layer ETL, the electron transport layer ETL may have a composition of about

To about->

Is a thickness of (c). For example, the electron transport layer ETL may have about +.>

To about->

Is a thickness of (c). When the thickness of the electron transport layer ETL satisfies the above-described range, satisfactory electron transport properties can be obtained without a significant increase in the driving voltage. When the electron transport region ETR includes an electron injection layer EIL, the electron injection layer EIL may have about +. >

To about

Is a thickness of (c). For example, the electron injection layer EIL may have about +.>

To about->

Is a thickness of (c). When the thickness of the electron injection layer EIL satisfies the above-described range, satisfactory electron injection properties can be obtained without a significant increase in the driving voltage.

The second electrode EL2 is provided on the electron transport region ETR. The second electrode EL2 may be a common electrode. The second electrode EL2 may be a cathode or an anode, but the embodiment is not limited thereto. For example, when the first electrode EL1 is an anode, the second electrode EL2 may be a cathode; and when the first electrode EL1 is a cathode, the second electrode EL2 may be an anode. The second electrode may comprise at least one of Ag, mg, cu, al, pt, pd, au, ni, nd, ir, cr, li, ca, liF, mo, ti, W, in, sn, zn, an oxide thereof, a compound thereof, and a mixture thereof.

The second electrode EL2 may be a transmissive electrode, a transflective electrode, or a reflective electrode. When the second electrode EL2 is a transmissive electrode, the second electrode EL2 may include a transparent metal oxide, for example, indium Tin Oxide (ITO), indium Zinc Oxide (IZO), zinc oxide (ZnO), indium Tin Zinc Oxide (ITZO), or the like.

When the second electrode EL2 is a transflective electrode or a reflective electrode, the second electrode EL2 may contain Ag, mg, cu, al, pt, pd, au, ni, nd, ir, cr, li, ca, liF/Ca (a stacked structure of LiF and Ca), liF/Al (a stacked structure of LiF and Al), mo, ti, yb, W, a compound thereof, or a mixture thereof (for example, agMg, agYb, or MgYb). In another embodiment, the second electrode EL2 may have a multilayer structure including a reflective film or a transflective film formed of the above-described material, and a transmissive conductive film formed of Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), zinc oxide (ZnO), indium Tin Zinc Oxide (ITZO), or the like. For example, the second electrode EL2 may contain the above-described metal material, a combination of two or more metal materials selected from the above-described metal materials, or an oxide of the above-described metal material.

Although not shown in the drawings, the second electrode EL2 may be electrically connected to the auxiliary electrode. When the second electrode EL2 is electrically connected to the auxiliary electrode, the resistance of the second electrode EL2 can be reduced.

In an embodiment, the light emitting element ED may further include a cover layer CPL provided on the second electrode EL 2. The cover layer CPL may be a plurality of layers or a single layer.

In an embodiment, the capping layer CPL may include an organic layer or an inorganic layer. For example, when the cover layer CPL contains an inorganic material, there is noThe organic material may include alkali metal compounds (e.g., liF), alkaline earth metal compounds (e.g., mgF) ₂ ) SiO _x N _y 、SiN _x 、SiO _y Etc.

For example, when the capping layer CPL comprises an organic material, the organic material may include alpha-NPD, NPB, TPD, m-MTDATA, alq ₃ CuPc, N4' -tetra (biphenyl-4-yl) biphenyl-4, 4' -diamine (TPD 15), 4',4 "-tris (carbazol-9-yl) triphenylamine (TCTA), etc., or may comprise an epoxy-based resin or an acrylate such as a methacrylate. However, the embodiment is not limited thereto, and the capping layer CPL may contain at least one of the compounds P1 to P5.

The refractive index of the capping layer CPL may be equal to or greater than about 1.6. For example, the refractive index of the capping layer CPL may be equal to or greater than about 1.6 with respect to light in the wavelength range of about 550nm to about 660 nm.

Fig. 8 to 11 are each a schematic cross-sectional view of a display device according to an embodiment. In the description of the display device according to the embodiment with reference to fig. 8 and 11, features that have been described with reference to fig. 1 to 7 will not be described again, and the description will focus on different features.

Referring to fig. 8, a display device DD-a according to an embodiment may include a display panel DP including a display element layer DP-ED, a light control layer CCL disposed on the display panel DP, and a color filter layer CFL.

In the embodiment illustrated in fig. 8, the display panel DP may include a base layer BS, a circuit layer DP-CL provided on the base layer BS, and a display element layer DP-ED, and the display element layer DP-ED may include a light emitting element ED.

The light emitting element ED may include a first electrode EL1, a hole transporting region HTR disposed on the first electrode EL1, a light emitting layer EML disposed on the hole transporting region HTR, an electron transporting region ETR disposed on the light emitting layer EML, and a second electrode EL2 disposed on the electron transporting region ETR. The structure of the light emitting element ED illustrated in fig. 8 may be the same as that of the light emitting element according to one of fig. 3 to 7.

The hole transport region HTR of the light emitting element ED included in the display device DD-a according to the embodiment may include the amine compound according to the embodiment described above.

Referring to fig. 8, the light emitting layer EML may be disposed in an opening OH defined in the pixel defining layer PDL. For example, light emitting layers EML separated by the pixel defining layer PDL and provided corresponding to the light emitting areas PXA-R, PXA-G and PXA-B, respectively, may emit light within the same wavelength range. In the display device DD-a according to the embodiment, the light emitting layer EML may emit blue light. Although not shown in the drawings, in an embodiment, the light emitting layer EML may be provided as a common layer for all light emitting areas PXA-R, PXA-G and PXA-B.

The light control layer CCL may be disposed on the display panel DP. The light control layer CCL may comprise a light converter. The light converter may be a quantum dot, phosphor, or the like. The light converter may convert the wavelength of the provided light and may emit the resulting light. For example, the light control layer CCL may be a layer containing quantum dots or a layer containing phosphor.

The light control layer CCL may include light control components CCP1, CCP2, and CCP3. The light control parts CCP1, CCP2 and CCP3 may be separated from each other.

Referring to fig. 8, the division pattern BMP may be disposed between the separate light control parts CCP1, CCP2, and CCP3, but the embodiment is not limited thereto. Fig. 8 illustrates that the separation pattern BMP does not overlap the light control members CCP1, CCP2, and CCP3, but edges of the light control members CCP1, CCP2, and CCP3 may overlap at least a portion of the separation pattern BMP.

The light control layer CCL may include a first light control member CCP1 including first quantum dots QD1 converting first color light provided by the light emitting element ED into second color light, a second light control member CCP2 including second quantum dots QD2 converting the first color light into third color light, and a third light control member CCP3 transmitting the first color light.

In an embodiment, the first light control part CCP1 may provide red light as the second color light, and the second light control part CCP2 may provide green light as the third color light. The third light control part CCP3 may transmit blue light as the first color light provided by the light emitting element ED. For example, the first quantum dot QD1 may be a red quantum dot and the second quantum dot QD2 may be a green quantum dot. The same explanation as provided above for the quantum dots may be applied for the quantum dots QD1 and QD2.

The light control layer CCL may further comprise a diffuser SP. The first light control member CCP1 may include first quantum dots QD1 and a diffuser SP, the second light control member CCP2 may include second quantum dots QD2 and a diffuser SP, and the third light control member CCP3 may include no quantum dots but may include a diffuser SP.

The scatterers SP may be inorganic particles. For example, the diffuser SP may include TiO ₂ 、ZnO、Al ₂ O ₃ 、SiO ₂ And at least one of hollow silica. The scatterer SP may comprise TiO ₂ 、ZnO、Al ₂ O ₃ 、SiO ₂ And hollow silica, or the scatterer SP may be selected from TiO ₂ 、ZnO、Al ₂ O ₃ 、SiO ₂ And mixtures of two or more materials in the hollow silica.

The first, second and third light control members CCP1, CCP2 and CCP3 may include matrix resins BR1, BR2 and BR3 for dispersing the quantum dots QD1 and QD2 and the scatterers SP, respectively. In an embodiment, the first light control member CCP1 may include first quantum dots QD1 and a diffuser SP dispersed in a first matrix resin BR1, the second light control member CCP2 may include second quantum dots QD2 and a diffuser SP dispersed in a second matrix resin BR2, and the third light control member CCP3 may include a diffuser SP dispersed in a third matrix resin BR3. The matrix resins BR1, BR2, and BR3 may each be a medium in which the quantum dots QD1 and QD2 and the scatterer SP are dispersed, and may be composed of various resin compositions, which may be generally referred to as binders. For example, the matrix resins BR1, BR2, and BR3 may be acrylic-based resins, urethane-based resins, silicone-based resins, or epoxy-based resins, or the like. The matrix resins BR1, BR2, and BR3 may be transparent resins. In an embodiment, the first, second, and third matrix resins BR1, BR2, and BR3 may be the same or different from each other.

The light control layer CCL may include a barrier layer BFL1. The barrier layer BFL1 may block permeation of moisture and/or oxygen (hereinafter, referred to as "moisture/oxygen"). The blocking layer BFL1 may be disposed on the light control members CCP1, CCP2, and CCP3 to block the light control members CCP1, CCP2, and CCP3 from being exposed to moisture/oxygen. The blocking layer BFL1 may cover the light control components CCP1, CCP2, and CCP3. The blocking layer BFL2 may be provided between the light control parts CCP1, CCP2 and CCP3 and the filters CF1, CF2 and CF 3.

The barrier layers BFL1 and BFL2 may include at least one inorganic layer. For example, the barrier layers BFL1 and BFL2 may be formed by comprising an inorganic material. For example, the barrier layers BFL1 and BFL2 may each independently include silicon nitride, aluminum nitride, zirconium nitride, titanium nitride, hafnium nitride, tantalum nitride, silicon oxide, aluminum oxide, titanium oxide, tin oxide, cerium oxide, silicon oxynitride, or a metal thin film having sufficient light transmittance, or the like. The barrier layers BFL1 and BFL2 may further comprise an organic film. The barrier layers BFL1 and BFL2 may be formed from a single layer or from multiple layers.

In the display device DD-a according to an embodiment, a color filter layer CFL may be disposed on the light control layer CCL. In an embodiment, the color filter layer CFL may be disposed directly on the light control layer CCL. For example, the barrier layer BFL2 may be omitted.

The color filter layer CFL may include filters CF1, CF2, and CF3. The color filter layer CFL may include a first filter CF1 transmitting the second color light, a second filter CF2 transmitting the third color light, and a third filter CF3 transmitting the first color light. For example, the first filter CF1 may be a red filter, the second filter CF2 may be a green filter, and the third filter CF3 may be a blue filter. Each of the filters CF1, CF2, and CF3 may contain a polymer photosensitive resin, and a pigment or dye. The first filter CF1 may contain a red pigment or dye, the second filter CF2 may contain a green pigment or dye, and the third filter CF3 may contain a blue pigment or dye. However, the embodiment is not limited thereto, and the third filter CF3 may not include pigment or dye. The third filter CF3 may contain a polymeric photosensitive resin and may not contain a pigment or dye. The third filter CF3 may be transparent. The third filter CF3 may be formed of a transparent photosensitive resin.

In an embodiment, the first filter CF1 and the second filter CF2 may each be a yellow filter. The first filter CF1 and the second filter CF2 may not be separated from each other and provided as a single filter. The first to third filters CF1, CF2 and CF3 may be disposed to correspond to each of the red, green and blue light emitting areas PXA-R, PXA-G and PXA-B, respectively.

Although not shown in the drawings, the color filter layer CFL may include a light blocking member (not shown). The color filter layer CFL may include a light blocking member (not shown) disposed to overlap boundaries between adjacent filters CF1, CF2, and CF3. The light blocking member (not shown) may be a black matrix. The light blocking member (not shown) may include an organic light blocking material or an inorganic light blocking material, which includes a black pigment or a black dye. The light blocking member (not shown) may divide adjacent filters CF1, CF2, and CF3. In an embodiment, the light blocking member (not shown) may be formed of a blue filter.

The base substrate BL may be disposed on the color filter layer CFL. The base substrate BL may provide a base surface on which the color filter layer CFL and the light control layer CCL are disposed. The base substrate BL may be a glass substrate, a metal substrate, a plastic substrate, or the like. However, the embodiment is not limited thereto, and the base substrate BL may include an inorganic layer, an organic layer, or a composite material layer. Although not shown in the drawings, in an embodiment, the base substrate BL may be omitted.

Fig. 9 is a schematic cross-sectional view illustrating a portion of a display device according to an embodiment. Fig. 9 illustrates a schematic cross-sectional view of a portion corresponding to the display panel DP in fig. 8.

In the display device DD-TD according to the embodiment, the light emitting elements ED-BT may include light emitting structures OL-B1, OL-B2, and OL-B3. The light emitting element ED-BT may include a first electrode EL1 and a second electrode EL2 facing each other, and light emitting structures OL-B1, OL-B2, and OL-B3 stacked in a thickness direction and provided between the first electrode EL1 and the second electrode EL 2. Each of the light emitting structures OL-B1, OL-B2, and OL-B3 may include a light emitting layer EML (fig. 8), and a hole transporting region HTR and an electron transporting region ETR (fig. 8) between which the light emitting layer EML is disposed.

For example, the light emitting elements ED to BT included in the display device DD to TD according to the embodiment may be light emitting elements having a series structure including a plurality of light emitting layers.

In the embodiment illustrated in fig. 9, the light emitted from each of the light emitting structures OL-B1, OL-B2, and OL-B3 may be all blue light. However, the embodiment is not limited thereto, and wavelength ranges of light emitted by the light emitting structures OL-B1, OL-B2, and OL-B3 may be different from each other. For example, the light emitting elements ED-BT including the light emitting structures OL-B1, OL-B2 and OL-B3 emitting light in different wavelength ranges may emit white light.

The charge generation layers CGL1 and CGL2 may be disposed between adjacent light emitting structures OL-B1, OL-B2, and OL-B3. The charge generation layers CGL1 and CGL2 may each independently include a p-type charge generation layer and/or an n-type charge generation layer.

At least one of the light emitting structures OL-B1, OL-B2, and OL-B3 included in the display device DD-TD according to the embodiment may contain the amine compound according to the embodiment described above.

Referring to fig. 10, a display device DD-b according to an embodiment may include light emitting elements ED-1, ED-2, and ED-3 each including two light emitting layers stacked. The display device DD-b according to the embodiment illustrated in fig. 10 may be different from the display device DD according to the embodiment illustrated in fig. 2 at least in that: the light emitting elements ED-1, ED-2, and ED-3 in the display device DD-b in FIG. 10 each include two light emitting layers stacked in the thickness direction. In each of the first to third light emitting elements ED-1, ED-2 and ED-3, the two light emitting layers may emit light of the same wavelength range.

The first light emitting element ED-1 may include a first red light emitting layer EML-R1 and a second red light emitting layer EML-R2. The second light emitting element ED-2 may include a first green light emitting layer EML-G1 and a second green light emitting layer EML-G2. The third light emitting element ED-3 may include a first blue light emitting layer EML-B1 and a second blue light emitting layer EML-B2. The light emission assisting member OG may be disposed between the first and second red light emitting layers EML-R1 and EML-R2, between the first and second green light emitting layers EML-G1 and EML-G2, and between the first and second blue light emitting layers EML-B1 and EML-B2.

The light emission assisting member OG may be a single layer or a plurality of layers. The light emission assisting member OG may include a charge generating layer. For example, the light emission assisting member OG may include an electron transport region, a charge generation layer, and a hole transport region stacked in this order. The light emission assisting part OG may be provided as a common layer of all the first to third light emitting elements ED-1, ED-2 and ED-3. However, the embodiment is not limited thereto, and the light emission assisting member OG may be provided by patterning in the opening OH defined in the pixel defining layer PDL.

The first red light emitting layer EML-R1, the first green light emitting layer EML-G1, and the first blue light emitting layer EML-B1 may be each disposed between the electron transport region ETR and the light emission auxiliary member OG. The second red light emitting layer EML-R2, the second green light emitting layer EML-G2, and the second blue light emitting layer EML-B2 may be each disposed between the light emission auxiliary part OG and the hole transport region HTR.

For example, the first light emitting element ED-1 may include a first electrode EL1, a hole transport region HTR, a second red emission layer EML-R2, an emission assistance part OG, a first red emission layer EML-R1, an electron transport region ETR, and a second electrode EL2 stacked in this order. The second light emitting element ED-2 may include a first electrode EL1, a hole transporting region HTR, a second green light emitting layer EML-G2, a light emitting auxiliary part OG, a first green light emitting layer EML-G1, an electron transporting region ETR, and a second electrode EL2 stacked in this order. The third light emitting element ED-3 may include a first electrode EL1, a hole transporting region HTR, a second blue light emitting layer EML-B2, a light emitting auxiliary part OG, a first blue light emitting layer EML-B1, an electron transporting region ETR, and a second electrode EL2 stacked in this order.

The optical auxiliary layer PL may be disposed on the display element layer DP-ED. The optical auxiliary layer PL may include a polarizing layer. The optical auxiliary layer PL may be disposed on the display panel DP and may control light reflected at the display panel DP by external light. Although not shown in the drawings, in an embodiment, the optical auxiliary layer PL may be omitted from the display device DD-b.

Fig. 11 illustrates a display device DD-C differing at least in that it comprises four light emitting structures OL-B1, OL-B2, OL-B3 and OL-C1, compared to fig. 9 and 10. The light emitting element ED-CT may include first and second electrodes EL1 and EL2 facing each other, and first to fourth light emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 stacked in a thickness direction and provided between the first and second electrodes EL1 and EL 2. The charge generation layers CGL1, CGL2, and CGL3 may be disposed between the first to fourth light emitting structures OL-B1, OL-B2, OL-B3, and OL-C1. Of the four light emitting structures, the first to third light emitting structures OL-B1, OL-B2 and OL-B3 may each emit blue light, and the fourth light emitting structure OL-C1 may emit green light. However, the embodiment is not limited thereto, and the first to fourth light emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 may emit light in wavelength ranges different from each other.

The charge generation layers CGL1, CGL2, and CGL3 disposed between adjacent light emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 may each independently include a p-type charge generation layer and/or an n-type charge generation layer.

At least one of the light emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 included in the display device DD-C according to the embodiment may contain the amine compound according to the embodiment described above.

The light emitting element ED according to the embodiment may contain the amine compound according to the embodiment described above in at least one functional layer provided between the first electrode EL1 and the second electrode EL2, thereby exhibiting improved light emitting efficiency and lifetime characteristics. The light-emitting element ED according to the embodiment may contain the amine compound according to the embodiment described above in at least one of the hole transport region HTR, the light-emitting layer EML, and the electron transport region ETR, or may contain the amine compound described in the capping layer CPL.

For example, the amine compound according to the embodiment may be included in the hole transport region HTR of the light emitting element ED according to the embodiment, and the light emitting element ED according to the embodiment may exhibit excellent light emitting efficiency and long service life characteristics.

The amine compound according to the embodiment described above may exhibit improved service life characteristics by containing a dibenzo-dicyclopentadiene moiety protected by a naphthyl group having excellent heat resistance and charging resistance. In the embodiment, since the bonding positions of the dibenzo-heterocyclopentadiene group and the naphthyl group are specified, the symmetry of the amine compound molecule is reduced, so that the crystallinity of the amine compound molecule is suppressed, and thus the hole transporting property of the amine compound according to the embodiment can be improved. Accordingly, the light-emitting efficiency of the light-emitting element including the amine compound according to the embodiment can be improved.

Hereinafter, an amine compound according to an embodiment and a light emitting element according to an embodiment will be described in detail with reference to examples and comparative examples. The embodiments illustrated below are provided merely as examples to aid in understanding the present disclosure, and the scope of the present disclosure is not limited thereto.

Examples (example)

1. Synthesis of amine Compounds

The method of synthesizing the amine compound according to the embodiment will be explained by describing the method of synthesizing compound 3, compound 5, compound 14, compound 19, compound 45, compound 52, compound 67, and compound 81. The synthetic methods of the amine compounds described below are merely examples, and the synthetic methods of the compounds according to the embodiments are not limited to the examples.

(1) Synthesis of Compound 3

The aromatic compound 3 according to the embodiment may be synthesized, for example, by the process of the following reaction scheme.

< Synthesis of intermediate A >

[ reaction type 1-1]

1-bromo-4-iodobenzofuran (25 g,67 mmol), 2-naphthaleneboronic acid (312.6 g,73.7 mmol), tetrakis (triphenylphosphine) palladium (0) (4.6 g,4 mmol) and K ₂ CO ₃ (28 g,201 mmol) was added to a mixed solution of 268mL of toluene, 134mL of ethanol and 67mL of water, and after degassing, the resulting mixture was heated at 85℃for 2 hours in an argon atmosphere. After cooling, the reaction solution was filtered and concentrated by Florisil, and the obtained residue was purified by column chromatography. After purification, intermediate A (20 g,53 mmol) was obtained.

< Synthesis of intermediate B >

[ reaction type 1-2]

In 4- (naphthalen-2-yl) aniline (8 g,41 mmol), intermediate A (16.7 g,45 mmol), pd (dba) ₂ (1.17g，2.03mmol)、P(tBu) ₃ H+BF ₄ After degassing of- (2.36 g,8.14 mmol) and NaO (tBu) (3.91 g,40.68 mmol), 407mL of toluene was added dropwise to the reaction solution under argon and heated at 80℃for 2 hours. After cooling, the reaction solution was filtered and concentrated by Florisil, and the obtained residue was purified by column chromatography to obtain intermediate B (16.7 g,33 mmol).

< Synthesis of Compound 3 >

[ reaction type 1-3]

4-bromodibenzothiophene (7.9 g, 30 mmol), intermediate B (14 g,27 mmol), pd (dba) ₂ (0.78g，1.36mmol)、P(tBu) ₃ H+BF ₄ - (1.74 g,6.0 mmol) and NaO (tBu) (5.22 g,54.34 mmol) were degassed, 272mL of toluene was added dropwise to the reaction solution heated at 80℃for 3 hours under an argon atmosphere. After cooling, the reaction solution was filtered and concentrated by Florisil, and the obtained residue was purified by column chromatography to obtain compound 3 (13.8 g,19.8 mmol).

FAB-MS measurements showed a molecular ion peak (m/z= 693.2), and therefore it was confirmed that the obtained compound was compound 3.

(2) Synthesis of Compound 5

Amine compound 5 according to the embodiment can be synthesized, for example, by the process of the following reaction scheme.

< Synthesis of intermediate C >

[ reaction type 2-1]

2-bromo-8-iodonaphthalene (25 g,75 mmol), phenylboronic acid (10.1 g,82.6 mmol), tetrakis (triphenylphosphine) palladium (0) (5.2 g,4.5 mmol) and K ₂ CO ₃ (31 g, 225 mmol) was added to a mixed solution of 300mL of toluene, 150mL of ethanol and 75mL of water, and after degassing, the resulting mixture was heated at 85℃for 2 hours in an argon atmosphere. After cooling, the reaction solution was filtered and concentrated by Florisil, and the obtained residue was purified by column chromatography to obtain intermediate C (17.4 g,62 mmol).

< Synthesis of intermediate D >

[ reaction type 2-2]

Intermediate C (17 g,60 mmol), 4-chlorophenyl boronic acid (10.3 g,66 mmol), tetra (triphenyl)Phosphine) palladium (0) (4.2 g,3.6 mmol) and K ₂ CO ₃ (24.9 g,180 mmol) was added to a mixed solution of 240mL of toluene, 120mL of ethanol and 60mL of water, and after degassing, the resulting mixture was heated at 85℃for 2 hours in an argon atmosphere. After cooling, the reaction solution was filtered and concentrated by Florisil, and the obtained residue was purified by column chromatography to obtain intermediate D (14.2 g,45 mmol).

< Synthesis of intermediate E >

[ reaction type 2-3]

Intermediate D (10 g,31.8 mmol), aniline (3.3 g,34.9 mmol), pd (dba) ₂ (0.91g，1.59mmol)、P(tBu) ₃ H+BF ₄ After degassing of- (1.84 g,6.35 mmol) and NaO (tBu) (3.05 g,31.77 mmol), 272mL of toluene were added dropwise to the reaction solution in an argon atmosphere and heated at 80℃for 3 hours. After cooling, the reaction solution was filtered and concentrated by Florisil, and the obtained residue was purified by column chromatography to obtain intermediate E (8.37 g,22.6 mmol).

< Synthesis of Compound 5 >

[ reaction type 2-4]

Intermediate E (5 g,13.5 mmol), intermediate A (5.53 g,14.8 mmol), pd (dba) ₂ (0.39g，0.67mmol)、P(tBu) ₃ H+BF ₄ After degassing of- (0.78 g,2.69 mmol) and NaO (tBu) (1.29 g,13.47 mmol), 134mL of toluene was added dropwise to the reaction solution heated at 80℃for 3 hours under an argon atmosphere. After cooling, the reaction solution was filtered and concentrated by Florisil, and the obtained residue was purified by column chromatography to obtain compound 5 (5.01 g,7.54mmol, yield 56%). FAB-MS measurement showed molecular ion peak (m/z= 663.3), and therefore it confirmed the obtained compound Is compound 5.

(3) Synthesis of Compound 14

Compound 14 was synthesized in the same manner as in the synthesis method of compound 3, except that 4-bromo-6-phenyl-dibenzothiophene was used instead of 4-bromodibenzothiophene in reaction formulae 1 to 3 of compound 3. Compound 14 was obtained in 32% yield. FAB-MS measurements show a molecular ion peak (m/z=769.2) and therefore it confirms that the compound obtained is compound 14.

(4) Synthesis of Compound 19

Compound 19 was synthesized in the same manner as in the synthesis method of compound 3, except that 1-bromo-4-iodobenzothiophene was used instead of 1-bromo-4-iodobenzofuran in reaction scheme 1-1 of compound 3 and 4-bromodibenzofuran was used instead of 4-bromodibenzothiophene in reaction scheme 1-3 of compound 3. Compound 19 was obtained in 48% yield. FAB-MS measurements showed a molecular ion peak (m/z= 693.3), and therefore it was confirmed that the obtained compound was compound 19.

(5) Synthesis of Compound 45

Compound 45 was synthesized in the same manner as in the synthesis method of compound 5, except that 1-bromo-8-iodonaphthalene was used instead of 2-bromo-8-iodonaphthalene in reaction formula 2-1 of compound 5 and 1-naphthylamine was used instead of aniline in reaction formula 2-3 of compound 5. Compound 45 was obtained in 51% yield. FAB-MS measurements showed a molecular ion peak (m/z= 713.3) and thus confirmed that the obtained compound was compound 45.

(6) Synthesis of Compound 52

Compound 52 was synthesized in the same manner as in the synthesis method of compound 3, except that 4-bromo-1-iodobenzofuran was used instead of 1-bromo-4-iodobenzofuran in reaction scheme 1-1 of compound 3 and 3-bromodibenzothiophene was used instead of 4-bromodibenzothiophene in reaction scheme 1-3 of compound 3. Compound 52 was obtained in 41% yield. FAB-MS measurements show a molecular ion peak (m/z= 693.2), and therefore it is confirmed that the obtained compound is compound 52.

(7) Synthesis of Compound 67

Compound 67 was synthesized in the same manner as in the synthesis method of compound 3, but 1-bromo-4-iodobenzofuran in reaction formula 1-1 of compound 3 was replaced with 1-bromo-4-iodo-9-phenyl-carbazole. Compound 67 was obtained in 18% yield. FAB-MS measurement showed a molecular ion peak (m/z= 768.3), and therefore it was confirmed that the obtained compound was compound 67.

(8) Synthesis of Compound 81

The amine compound 81 according to the embodiment may be synthesized, for example, by the process of the following reaction scheme.

< Synthesis of intermediate F >

[ reaction type 3-1]

4-bromo-1-iodobenzofuran (25 g,67 mmol), 2-naphthaleneboronic acid (312.6 g,73.7 mmol), tetrakis (triphenylphosphine) palladium (0) (4.6 g,4 mmol) and K ₂ CO ₃ (28 g,201 mmol) was added to a mixed solution of 268mL of toluene, 134mL of ethanol and 67mL of water, and after degassing, the resulting mixture was heated at 85℃for 2 hours in an argon atmosphere. After cooling, the reaction solution was filtered and concentrated by Florisil, and the obtained residue was purified by column chromatography. After purification, intermediate F (17.5 g,47 mmol) was obtained.

< Synthesis of Compound 81 >

[ reaction type 3-2]

In aniline (4 g,43 mmol), intermediate F (35.3 g,94.6 mmol), pd (dba) ₂ (1.24g，2.15mmol)、P(tBu) ₃ H+BF ₄ After degassing of- (2.5 g,8.6 mmol) and NaO (tBu) (4.13 g,43.0 mmol), 430mL of toluene were added dropwise to the reaction solution in an argon atmosphere and heated at 80℃for 2 hours. After cooling, the reaction solution was filtered and concentrated by Florisil, and the obtained residue was purified by column chromatography to obtain compound 81 (14.5 g,35.2 mmol). FAB-MS measurement showed molecular ion peak (m/z= 677.2), andit was therefore confirmed that the obtained compound was compound 81.

2. Manufacturing and evaluation of light emitting element

The evaluation of light-emitting elements including the compounds of examples and comparative examples in the hole transport layer was performed as described below. The following describes a method of manufacturing a light-emitting element for element evaluation.

(1) Manufacturing of light emitting element

Having been carried out by using isopropyl alcohol for about 5 minutes and pure water for about 5 minutes

An ITO patterned glass substrate of a thickness of (c) is ultrasonically cleaned. After the ultrasonic cleaning, the glass substrate was irradiated with UV rays for 30 minutes and subjected to ozone treatment. Thereafter, the compounds HT1 and HIL were deposited to +.2 in a weight ratio of 98:2>

To form a hole injection layer.

Deposition of Compound HT1 to

To form a first hole transport layer. In examples 1 to 8 and comparative examples 1 to 5, the example compound or the comparative example compound was deposited to +.>

To form a second hole transport layer.

Thereafter, the host (E2) and dopant (BD) were co-deposited at a weight ratio of 98:2 to form a semiconductor device having

Is a light-emitting layer of a thickness of (a). Sequentially deposit->

ET1 and +.>

ET2 to form an electron transport layer and depositing LiF to +.>

To form an electron injection layer.

Forming the second electrode into a shape by using Ag and Mg in a weight ratio of 10:90

Is a thickness of (c).

In an embodiment, the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer, the electron injection layer, and the second electrode are formed using a vacuum deposition apparatus.

Example compounds and comparative example compounds for manufacturing light emitting elements are as follows.

< example Compound >

< comparative example Compound >

The compounds of the respective functional layers are as follows.

(2) Evaluation of light-emitting element

Table 1 shows the evaluation results of the light emitting elements according to examples 1 to 8 and comparative examples 1 to 5. Table 1 shows the production by comparison between examples and comparative examples The luminous efficiency and the service life of the luminous element. In the results of characteristic evaluation of examples and comparative examples shown in Table 1, luminous efficiency was expressed at 25mA/cm ² Is shown at a current density of 10mA/cm ² The luminance half-life under.

In table 1, the light-emitting efficiency and the service life characteristics are shown as relative values obtained when the light-emitting efficiency and the service life of comparative example 1 are each 100%.

TABLE 1

Referring to the results of table 1, it can be confirmed that examples in which the light-emitting element uses the amine compound according to the embodiment as a material of the hole transport layer exhibit excellent light-emitting efficiency and improved element lifetime characteristics. Referring to table 1, it can be seen that the light emitting elements of examples 1 to 8 exhibited long service life and high light emitting efficiency characteristics as compared with the light emitting elements of comparative examples 1 to 5. Since the amine compound according to the example includes a dibenzo-dicyclopentadiene moiety in which a naphthalene group is substituted, it can be confirmed that high luminous efficiency and long service life characteristics are exhibited as compared with the amine compound of the comparative example. Among the amine compounds used in examples 1 to 8, since the naphthyl group was substituted at the 4-position of dibenzocyclopentadiene, the heteroatom was protected by the naphthyl group and less affected by electrons. Therefore, it is considered that the service life of the light-emitting element using the amine compound of the embodiment is improved. In the amine compound used in the examples, the substitution position of the naphthyl group on the dibenzocyclopentadiene is para to the nitrogen atom of the amine, so that the symmetry of the molecule of the amine compound is reduced and thus the crystallinity is suppressed to improve hole transport property. Therefore, the light emitting element according to the embodiment is considered to exhibit high light emitting efficiency characteristics.

In comparison with the examples, the comparative example compound c1 used in comparative example 1 has a dibenzo-dicyclopentadiene moiety in which a naphthalene group is substituted similar to the amine compound of the example. However, the comparative example compound c1 is different from the compound of the example in the substitution position of the naphthyl group, because the naphthyl group is substituted at the meta position of the dibenzocyclopentadiene moiety with respect to the nitrogen atom of the amine compound. Due to the difference in the substitution positions of the naphthyl groups, in the comparative example compound c1, the Highest Occupied Molecular Orbital (HOMO) was not wide enough, and the electron density on the amine side was relatively increased. Accordingly, deterioration of the compound is accelerated, and thus the comparative example compound c1 is considered to exhibit a lower life characteristic than the example compound.

The comparative example compound c2 used in comparative example 2 is a compound having a dibenzo-dicyclopentadiene moiety in which a naphthyl group is substituted similarly to the example compound, but differs from the example compound in that the naphthyl group is not included in other substituents of the amine. Therefore, it is considered that the hetero atom of the dibenzocyclopentadiene moiety in the comparative example compound c2 is not sufficiently protected by the naphthyl group, and is thus easily affected by electrons, resulting in a decrease in luminous efficiency and element lifetime.

The comparative example compound c3 used in comparative example 3 does not include a dibenzo-cyclopentadiene moiety, and thus has high molecular symmetry, and thus the crystallinity increases. Therefore, it is considered that the light-emitting efficiency and the service life of comparative example 3 are reduced. Comparative example 4 uses the comparative example compound c4 containing no naphthyl group and having insufficient hole transport property, thereby exhibiting significantly reduced service life characteristics.

The comparative example compound c5 used in comparative example 5 contains a phenanthryl group as one of substituents of the amine compound, and crystallinity increases due to high flatness of the phenanthryl group. Therefore, the light-emitting efficiency and the service life of comparative example compound 5 are considered to be reduced.

The amine compound according to an embodiment comprises at least one dibenzo-dicyclopentadiene moiety in which the dibenzo-dicyclopentadiene moiety is substituted with a naphthyl group, and has a structure in which the naphthyl group is substituted at a position capable of protecting the dibenzo-dicyclopentadiene moiety. Therefore, when an amine compound is used as a material of the light-emitting element, the light-emitting efficiency of the light-emitting element and the element lifetime can be improved.

The light emitting element according to the embodiment may include the amine compound according to the embodiment, and thus exhibit high light emitting efficiency and long service life characteristics.

The amine compound according to the embodiment can be used as a material for achieving improved characteristics of a light-emitting element having high light-emitting efficiency and long service life.

Embodiments have been disclosed herein, and although terminology is used, they are used and described in a generic and descriptive sense only and not for purposes of limitation. In some cases, features, characteristics, and/or elements described with respect to an embodiment may be used alone or in combination with features, characteristics, and/or elements described with respect to other embodiments, unless specifically indicated otherwise, as will be apparent to one of ordinary skill in the art. Accordingly, it will be understood by those of ordinary skill in the art that various changes in form and details may be made therein without departing from the spirit and scope of the present disclosure as set forth in the following claims.

Claims

1. An amine compound represented by formula 1:

[ 1]

[ 2]

Wherein in the formula 1,

Ar ₁ is a substituted or unsubstituted aryl group having 6 to 40 ring-forming carbon atoms other than a phenanthryl group, or a substituted or unsubstituted aryl group havingHeteroaryl groups having 5 to 40 ring-forming carbon atoms,

R ₁ to R ₄ Each independently is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 ring-forming carbon atoms, or a single bond forming a ring by bonding to a group represented by formula 2, and

R ₁ And R is ₂ R and/or R of (C) ₃ And R is ₄ Is bonded to the group represented by formula 2 to form a ring,

wherein in the formula 2,

x is O, S, N (R) ₁₀ ) Or C (R) ₁₁ )(R ₁₂ ) And (b)

a and b each represent R in formula 1 ₁ To R ₄ One of the keys

Wherein in the formulas 1 and 2,

R ₅ to R ₁₂ Each independently is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 40 ring-forming carbon atoms,

a and b are each independently integers from 0 to 2,

c and d are each independently integers from 0 to 7, and

e is an integer from 0 to 4.

2. The amine compound according to claim 1, wherein the amine compound represented by formula 1 is represented by one of formulas 1-1 to 1-3:

[ 1-1]

[ 1-2]

[ 1-3]

Wherein in the formulae 1 to 3,

X ₁ and X ₂ Each independently is O, S, N (R ₁₀ ) Or C (R) ₁₁ )(R ₁₂ )，

e1 and e2 are each independently integers from 0 to 4, and

R ₉₁ and R is ₉₂ Each independently is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 40 ring-forming carbon atoms, and

wherein in the formulae 1-1 to 1-3,

Ar ₁ 、X、R ₁ 、R ₂ 、R ₅ to R ₁₂ And a to e are the same as defined in formulae 1 and 2.

3. The amine compound according to claim 2, wherein in the formulae 1 to 3,

X ₁ and X ₂ The same applies.

4. The amine compound according to claim 1, wherein the group represented by formula 2 is represented by one of formulas 2-1 to 2-5:

wherein in the formulae 2-1 to 2-5,

R ₉ e, a and b are the same as defined in formula 2.

5. The amine compound according to claim 1, wherein in formula 1,

Ar ₁ is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl groupA substituted or unsubstituted dibenzothiophene group, or a substituted or unsubstituted dibenzofuran group.

6. The amine compound according to claim 1, wherein in the formulas 1 and 2,

R ₁ to R ₉ At least one of which is a deuterium atom or a substituent comprising a deuterium atom; and/or Ar ₁ Is a substituent comprising a deuterium atom.

7. The amine compound according to claim 1, wherein the amine compound represented by formula 1 is a monoamine compound.

8. The amine compound of claim 1, wherein the amine compound is selected from compound group 1:

[ Compound group 1]

Wherein in the group of compounds 1,

d represents a deuterium atom.

9. A light emitting element comprising:

a first electrode;

A second electrode disposed on the first electrode; and

at least one functional layer arranged between the first electrode and the second electrode and comprising an amine compound according to any one of claims 1 to 8.

10. The light-emitting element according to claim 9, wherein

The at least one functional layer comprises:

a light emitting layer;

a hole transport region disposed between the first electrode and the light emitting layer; and

an electron transport region disposed between the light emitting layer and the second electrode, and the hole transport region contains the amine compound.

11. The light-emitting element according to claim 10, wherein

The hole transport region includes at least one of a hole injection layer, a hole transport layer, and an electron blocking layer, an

The at least one of the hole injection layer, the hole transport layer, and the electron blocking layer contains the amine compound.

12. The light-emitting element according to claim 10, wherein

The hole transport region includes a first hole transport layer and a second hole transport layer stacked in order between the first electrode and the light emitting layer,

the first hole transport layer and the second hole transport layer comprise different hole transport materials, an

The second hole transport layer includes the amine compound.

13. The light-emitting element according to claim 10, wherein the light-emitting layer comprises a compound represented by formula E-1:

[ E-1]

Wherein in the formula E-1, the amino acid sequence,

c and d are each independently integers from 0 to 5,

R ₃₁ to R ₄₀ Each independently is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, or is bonded to an adjacent group to form a ring.

14. The light-emitting element according to claim 9, further comprising:

a cover layer disposed on the second electrode, wherein

The cover layer has a refractive index equal to or greater than 1.6.